4-Pyridinemethanamine → (S)-6,6-Dimethyl-4-{[(pyridin-4-ylmethyl)-carbamoyl]-methyl}-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552247Notes

Reaction equation

HRID 552247 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]([OH:27])=O)[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][CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=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:27])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=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 773174-PyridinemethanamineHCID 11384512[(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid

Product 1

HCID 11720347(S)-6,6-Dimethyl-4-{[(pyridin-4-ylmethyl)-carbamoyl]-methyl}-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 53%

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 4-(aminomethyl)pyridine. The product was isolated as hydrochloride salt in 53% yield. 1HNMR (300 MHz, D2O): δ 1.34 (s, 3H), 1.49 (s, 3H), 2.64 (d, 1H), 3.03 (d, 1H), 3.48 (d, 1H), 3.72 (t, 1H), 3.74 (d, 1H), 4.15-4.25 (m, 2H), 7.66 (d, 1H), 7.88 (s, 1H), 7.91 (s, 1H), 8.21(d, 1H), 8.44 (d,1H), 8.53 (d, 1H), 8.56 (s, 1H), 8.58 (s, 1H), 9.08 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.47 min. MS (M+H+): 507.3.

Sources & evidence

ORD record
ord-3da3ac3af66a4eac8495ea0fc60998f5
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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