Identification and Development of an Efficient Route to SB-649915

…, M Kingswood, M Loft, S Moore, S Smith…

Index: Armitage, Mark; Bret, Guillaume; Choudary, Bernie M.; Kingswood, Mike; Loft, Mike; Moore, Steve; Smith, Steve; Urquhart, Michael W. J. Organic Process Research and Development, 2012 , vol. 16, # 10 p. 1626 - 1634

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Citation Number: 6

Abstract

The discovery and development of an efficient manufacturing route to the SSRI-5-HT1A receptor antagonist 6-[(1-{2-[(2-methyl-5-quinolinyl) oxy] ethyl}-4-piperidinyl) methyl]-2 H-1, 4-benzoxazin-3 (4 H)-one (SB-649915) 1 is described. The existing route to 1 involved coupling quinoline 6 with piperidine 5 and was considered lengthy as a consequence of the nine synthetic steps required to prepare 5. Two new routes to the key piperidine ...

 Related Synthetic Route
p-Formylpyridine Structure

872-85-5

p-Formylpyridine

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

4-(p-Methoxybenzyl)pyridine Structure

35854-35-4

4-(p-Methoxyben...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

tert-butyl 4-(4-(2-methoxy-2-oxoethoxy)-3-nitrobenzyl)piperidine-1-carboxylate Structure

420786-56-7

tert-butyl 4-(4...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

4-(pyridin-4-ylmethyl)phenol Structure

66414-18-4

4-(pyridin-4-yl...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

4-(piperidin-4-ylmethyl)phenol Structure

66414-17-3

4-(piperidin-4-...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

1-(furan-2-yl)-2,2-dimethylpropan-1-one Structure

420786-66-9

1-(furan-2-yl)-...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

4-Bromoanisole Structure

104-92-7

4-Bromoanisole

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

2-nitro-4-(piperidin-4-ylmethyl)phenol Structure

583031-16-7

2-nitro-4-(pipe...

~%

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

2-[(2-methyl-5-quinolinyl)oxy]ethyl methanesulfonate Structure

1399854-50-2

2-[(2-methyl-5-...

N/A Structure

1399854-47-7

N/A

~84%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

5-(2-bromoethoxy)-2-methylquinoline Structure

420786-70-5

5-(2-bromoethox...

6-(PIPERIDIN-4-YLMETHYL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE Structure

742051-67-8

6-(PIPERIDIN-4-...

~56%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

5-Methoxy-2-methylquinoline Structure

79205-04-2

5-Methoxy-2-met...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

5-hydroxy-2-methylquinolinium bromide Structure

844903-57-7

5-hydroxy-2-met...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

2-[(2-methyl-5-quinolinyl)oxy]ethanol Structure

1399854-49-9

2-[(2-methyl-5-...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

p-Formylpyridine Structure

872-85-5

p-Formylpyridine

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

acetoaminophenol Structure

614-80-2

acetoaminophenol

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

4-bromo-2-(2-chloro-acetylamino)-phenol Structure

24036-48-4

4-bromo-2-(2-ch...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

2-Acetamido-4-bromophenol Structure

107986-49-2

2-Acetamido-4-b...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

aminophenol Structure

95-55-6

aminophenol

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

2-chloro-N-(2-hydroxyphenyl)acetamide Structure

10147-68-9

2-chloro-N-(2-h...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

Isonicotinic acid Structure

55-22-1

Isonicotinic acid

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

6-Bromo-2H-1,4-benzoxazin-3(4H)-one Structure

24036-52-0

6-Bromo-2H-1,4-...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

Isonicotinoyl chloride Structure

14254-57-0

Isonicotinoyl c...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

2-Amino-4-bromophenol Structure

40925-68-6

2-Amino-4-bromo...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

4-Bromoanisole Structure

104-92-7

4-Bromoanisole

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

2H-1,4-Benzoxazin-3(4H)-one Structure

5466-88-6

2H-1,4-Benzoxaz...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

ISONICOTINOYL CHLORIDE HYDROCHLORIDE Structure

39178-35-3

ISONICOTINOYL C...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

6-(1-pyridin-4-ylmethanoyl)-4H-benzo[1,4]oxazine-3-one hydrochloride Structure

1399854-48-8

6-(1-pyridin-4-...

~%

6-[(1-{2-[(2-Methyl-5-quinolinyl)oxy]ethyl}-4-piperidinyl)methyl] -2H-1,4-benzoxazin-3(4H)-one Structure

420785-70-2

6-[(1-{2-[(2-Me...

Isonicotinoyl chloride Structure

14254-57-0

Isonicotinoyl c...

~%

ISONICOTINOYL CHLORIDE HYDROCHLORIDE Structure

39178-35-3

ISONICOTINOYL C...

p-Formylpyridine Structure

872-85-5

p-Formylpyridine

~%

4-(piperidin-4-ylmethyl)phenol Structure

66414-17-3

4-(piperidin-4-...

4-Bromoanisole Structure

104-92-7

4-Bromoanisole

~%

4-(piperidin-4-ylmethyl)phenol Structure

66414-17-3

4-(piperidin-4-...


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