Piperidine → (S)-6,6-Dimethyl-4-(2-oxo-2-piperidin-1-yl-ethyl)morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552244Notes

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.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C([O-])(=O)C.[NH4+]>>[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])[N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

Reactant 3

HCID 8082Piperidine

HCID 517165Ammonium Acetate

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

Product 1

HCID 11605463(S)-6,6-Dimethyl-4-(2-oxo-2-piperidin-1-yl-ethyl)morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 90%

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 piperidine in 90% yield. 1H-NMR (300 MHz, DMSO-d6): δ 1.17 (s,3H), 1.29 (s,3H), 1.35-1.60 (m,6H), 2.25 (d,1H), 2.71 (d,1H), 3.15 (d,1H), 3.26 (dd,1H), 3.37 (dd,1H), 3.45-3.65 (m, 2H), 3.65 (d, 1H), 3.70 (m, 1H), 3.89 (m, 2H) 7.95 (d,1H), 8.15 (d,1H), 8.20 (d,1H), 8.37 (d,1H), 9.01 (s,1H), 10.43 (s,1H), 11.32 (s,1H). Retention Time (LC, method: ammonium acetate standard): 1.86 min. MS (M+H+): 484.3.

Workup

custom1.86 min

Sources & evidence

ORD record: ord-b72744dd59ae4704804fd3600c4eadb3
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951801B2

Reaction notes

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