6??(substituted phenyl)??5??methyl??4, 5??dihydro??pyridazin??3 (2H)??ones of medicinal interest. The synthesis of SK&F 94836 and SK&F 95654

…, J Mistry, MB Mitchell, KD Pancholi…

Index: Burpitt; Crawford; Davies; Mistry; Mitchell; Pancholi; Coates Journal of Heterocyclic Chemistry, 1988 , vol. 25, # 6 p. 1689 - 1695

Full Text: HTML

Citation Number: 14

Abstract

Abstract Two synthetic routes to the dihydropyridazinone-cyanoguanidine 4 (SK&F 94836) are described, both proceeding via the anilino compound 6. An efficient synthesis of the dihydropyridazinone-pyridone 5 (SK&F 95654) is reported. This synthesis proceeds via the fluoro-keto-acid 24, with subsequent displacement of the fluoro substituent by 4-pyridone. The surprising effectiveness of water as a solvent in this reaction has been highlighted.

 Related Synthetic Route
Acetanilide Structure

103-84-4

Acetanilide

~%

4-(4-Aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride Structure

120757-13-3

4-(4-Aminopheny...

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DIETHYL 2-(1-(4-ACETAMIDOPHENYL)-1-OXOPROPAN-2-YL)MALONATE Structure

81937-39-5

DIETHYL 2-(1-(4...

~%

4-(4-Aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride Structure

120757-13-3

4-(4-Aminopheny...

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N-[4-(2-chloropropanoyl)phenyl]acetamide Structure

81112-08-5

N-[4-(2-chlorop...

~%

4-(4-Aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride Structure

120757-13-3

4-(4-Aminopheny...

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6-(4-acetamidophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-27-6

6-(4-acetamidop...

~75%

6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-28-7

6-(4-Aminopheny...

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3-[4-(4-oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid Structure

113118-49-3

3-[4-(4-oxo-1,4...

~90%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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4H-pyran-4-one Structure

108-97-4

4H-pyran-4-one

6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-28-7

6-(4-Aminopheny...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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Benzenebutanoic acid,4-(acetylamino)-g-oxo Structure

5473-15-4

Benzenebutanoic...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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methyl 3-(4-acetamidobenzoyl)but-3-enoate Structure

120757-16-6

methyl 3-(4-ace...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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methyl 4-(4-aminophenyl)-4-oxo-3-(piperidin-1-ylmethyl)butanoate Structure

120757-15-5

methyl 4-(4-ami...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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3-(4-acetamidobenzoyl)-4-(N-piperidinyl)butanoic acid Structure

120757-14-4

3-(4-acetamidob...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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N-[4-(2-chloropropanoyl)phenyl]acetamide Structure

81112-08-5

N-[4-(2-chlorop...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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methyl 4-(4-acetamidophenyl)-3-methyl-4-oxobutanoate Structure

120757-17-7

methyl 4-(4-ace...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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DIETHYL 2-(1-(4-ACETAMIDOPHENYL)-1-OXOPROPAN-2-YL)MALONATE Structure

81937-39-5

DIETHYL 2-(1-(4...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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4-(4-Aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride Structure

120757-13-3

4-(4-Aminopheny...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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Acetanilide Structure

103-84-4

Acetanilide

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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4-Hydroxypyridine Structure

626-64-2

4-Hydroxypyridine

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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Fluorobenzene Structure

462-06-6

Fluorobenzene

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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2-chloro-1-(4-fluorophenyl)propan-1-one Structure

81112-09-6

2-chloro-1-(4-f...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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6-(4-acetamidophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-27-6

6-(4-acetamidop...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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4-Hydroxypyridine Structure

626-64-2

4-Hydroxypyridine

N/A Structure

52240-73-0

N/A

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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Chelidonic acid Structure

99-32-1

Chelidonic acid

6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-28-7

6-(4-Aminopheny...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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1,5-Bis(dimethylamino)-1,4-pentadien-3-one Structure

25299-40-5

1,5-Bis(dimethy...

6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one Structure

36725-28-7

6-(4-Aminopheny...

~%

4-methyl-3-[4-(4-oxopyridin-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one Structure

112127-66-9

4-methyl-3-[4-(...

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Acetanilide Structure

103-84-4

Acetanilide

~%

DIETHYL 2-(1-(4-ACETAMIDOPHENYL)-1-OXOPROPAN-2-YL)MALONATE Structure

81937-39-5

DIETHYL 2-(1-(4...

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methyl 3-(4-acetamidobenzoyl)but-3-enoate Structure

120757-16-6

methyl 3-(4-ace...

~%

4-(4-Acetamidophenyl)-3-methyl-4-oxobutanoic acid Structure

36725-26-5

4-(4-Acetamidop...

methyl 4-(4-acetamidophenyl)-3-methyl-4-oxobutanoate Structure

120757-17-7

methyl 4-(4-ace...

Learn More
Benzenebutanoic acid,4-(acetylamino)-g-oxo Structure

5473-15-4

Benzenebutanoic...

~%

4-(4-Acetamidophenyl)-3-methyl-4-oxobutanoic acid Structure

36725-26-5

4-(4-Acetamidop...

Learn More
methyl 4-(4-aminophenyl)-4-oxo-3-(piperidin-1-ylmethyl)butanoate Structure

120757-15-5

methyl 4-(4-ami...

~%

4-(4-Acetamidophenyl)-3-methyl-4-oxobutanoic acid Structure

36725-26-5

4-(4-Acetamidop...

Learn More
3-(4-acetamidobenzoyl)-4-(N-piperidinyl)butanoic acid Structure

120757-14-4

3-(4-acetamidob...

~%

4-(4-Acetamidophenyl)-3-methyl-4-oxobutanoic acid Structure

36725-26-5

4-(4-Acetamidop...

Learn More
Fluorobenzene Structure

462-06-6

Fluorobenzene

(2R)-2-Chloropropanoyl chloride Structure

7623-09-8

(2R)-2-Chloropr...

~92%

2-chloro-1-(4-fluorophenyl)propan-1-one Structure

81112-09-6

2-chloro-1-(4-f...

Learn More

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