e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Novel non-peptide nociceptin/orphanin fq receptor agonist, 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3 R)-3-piperidinyl]-1 H-benzimidazole: Design, synthesis, and …

…, Y Murata, K Ohashi, E Nakata

Index: Bruekelman, Stephen P.; Leach, (Miss) Susan E.; Meakins, G. Denis; Tirel, Malcolm D. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , p. 2801 - 2807

Full Text: HTML

Citation Number: 29

Abstract

... KCN, TsOH, H 2 O, 45 °C; (d) MeMgBr/THF, CH 2 Cl 2 , −78 °C to room temp; (e) NH 2 OH·HCl, EtOH/H 2 O, reflux; (f) 1-fluoro-2-nitrobenzene, K 2 CO 3 , CH 3 CN, reflux; (g) Zn, NH ... CH 2 Cl 2 , −30 °C to room temp; (b) AcOH, toluene, 100 °C; (c) 10% HCl in MeOH; (d) LAH, THF ...

N/A Structure

~59%

5-Ethyl-4-methylthiazol-2-amine Structure

5-Ethyl-4-methy...

2-(2,5-dimethylpyrrol-1-yl)-6-ethylpyridine Structure

2-(2,5-dimethyl...

~86%

6-Ethyl-2-pyridinamine Structure

6-Ethyl-2-pyrid...

1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrole Structure

1-(4-bromopheny...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

2-[4-(2,5-dimethylpyrrol-1-yl)benzilidene]-1,3-dithian Structure

2-[4-(2,5-dimet...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

2-(4-Aminophenyl)propanoicacid Structure

2-(4-Aminopheny...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

(4-Aminophenyl)acetic acid Structure

(4-Aminophenyl)...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzenecarbaldehyde Structure

4-(2,5-Dimethyl...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

2-[4-(2,5-dimethylpyrrol-1-yl)phenyl]propanoic acid Structure

2-[4-(2,5-dimet...

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

4-Bromoaniline Structure

~%

Ethyl 2-(4-aminophenyl)propanoate Structure

Ethyl 2-(4-amin...

N/A Structure

~85%

6-butylpyridin-2-amine Structure

6-butylpyridin-...

2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyridine Structure

2-(2,5-dimethyl...

~%

6-butylpyridin-2-amine Structure

6-butylpyridin-...

2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyridine Structure

2-(2,5-dimethyl...

methyl iodide Structure

~90%

2-(2,5-dimethylpyrrol-1-yl)-6-ethylpyridine Structure

2-(2,5-dimethyl...

Acetonylacetone Structure

Acetonylacetone

~%

2-(2,5-dimethylpyrrol-1-yl)-6-ethylpyridine Structure

2-(2,5-dimethyl...

Aminopicoline Structure

Acetonylacetone Structure

Acetonylacetone

~81%

2-(2,5-dimethylpyrrol-1-yl)-4-methylpyridine Structure

2-(2,5-dimethyl...

2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyridine Structure

2-(2,5-dimethyl...

~83%

2-Amino-6-picoline Structure

2-Amino-6-picoline

(4-Aminophenyl)acetic acid Structure

(4-Aminophenyl)...

Acetonylacetone Structure

Acetonylacetone

~87%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrole Structure

1-(4-bromopheny...

~%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzenecarbaldehyde Structure

4-(2,5-Dimethyl...

~%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

2-[4-(2,5-dimethylpyrrol-1-yl)benzilidene]-1,3-dithian Structure

2-[4-(2,5-dimet...

~%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

Acetonylacetone Structure

Acetonylacetone

~%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

4-Bromoaniline Structure

~%

[4-(2,5-DIMETHYL-1H-PYRROL-1-YL)PHENYL]-ACETIC ACID Structure

[4-(2,5-DIMETHY...

2,5-dimethyl-1-(4-methylthiazol-2-yl)pyrrole Structure

2,5-dimethyl-1-...

~63%

4-Methylthiazol-2-amine Structure

4-Methylthiazol...

2-(2,5-dimethylpyrrol-1-yl)-4-methylpyridine Structure

2-(2,5-dimethyl...

~80%

Aminopicoline Structure

1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrole Structure

1-(4-bromopheny...

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~73%

1-[1-(4-BROMOPHENYL)-2,5-DIMETHYL-1H-PYRROL-3-YL]-2,2,2-TRIFLUORO-1-ETHANONE Structure

1-[1-(4-BROMOPH...

1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrole Structure

1-(4-bromopheny...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~91%

4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzenecarbaldehyde Structure

4-(2,5-Dimethyl...

4-phenyl-2-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole Structure

4-phenyl-2-(2,5...

~61%

4-Phenyl-1,3-thiazol-2-amine Structure

4-Phenyl-1,3-th...

1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrole Structure

1-(4-bromopheny...

N,N-Dimethylacetamide Structure

N,N-Dimethylace...

~94%

n-(4-acetylphenyl)-2,5-dimethylpyrrole Structure

n-(4-acetylphen...

(2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylthiazol-5-yl)(phenyl)methanone Structure

(2-(2,5-dimethy...

~24%

(2-Amino-4-methyl-5-thiazolyl)phenylmethanoneoxime Structure

(2-Amino-4-meth...

Benzoyl chloride Structure

Benzoyl chloride

~%

(2-Amino-4-methyl-5-thiazolyl)phenylmethanoneoxime Structure

(2-Amino-4-meth...

N/A Structure

~63%

4-Methyl-5-phenyl-1,3-thiazol-2-amine Structure

4-Methyl-5-phen...

Protection of primary amines as N-substited 2, 5-dimethylpyr...

[Breukelman, Stephen P.; Meakins, G. Denis; Tirel, Malcolm D. Journal of the Chemical Society, Chemical Communications, 1982 , # 14 p. 800 - 801]