3-Aminopyridine → (S)-6,6-Dimethyl-4-(pyridin-3-ylcarbamoylmethyl)-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552246Notes

Reaction equation

HRID 552246 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@H:18]3[N:23]([CH2:24][C:25](O)=[O:26])[CH2:22][C:21]([CH3:29])([CH3:28])[O:20][CH2:19]3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[NH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@@H:18]3[CH2:19][O:20][C:21]([CH3:28])([CH3:29])[CH2:22][N:23]3[CH2:24][C:25](=[O:26])[NH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

3

Reactant 2

HCID 100093-AminopyridineHCID 11384512[(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid

Product 1

HCID 11691710(S)-6,6-Dimethyl-4-(pyridin-3-ylcarbamoylmethyl)-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 55%

Procedure

The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 3-aminopyridine. The product was isolated as hydrochloride salt in 55% yield. 1HNMR (300 MHz, D2O): δ 1.34 (s, 3H), 1.54 (s, 3H), 2.60 (d,1H), 3.4 (d, 1H), 3.50 (d, 1H), 3.70 (t, 1H), 3.81 (d, 1H) 4.23 (d, 2H), 7.69 (d, 1H), 7.98 (d, 1H), 8.01 (d, 1H), 8.17(d, 1H), 8.42 (d, 1H), 8.48-8.55 (m, 3H), 9.09 (s,1H), 9.30 (d, 1H). Retention Time (LC, method: ammonium acetate standard): 1.56 min. MS (M+H+): 493.2.

Sources & evidence

ORD record
ord-d7904b098ef146cbb19bfe4cf603412e
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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