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

HRID 552245Notes

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][O: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]([CH3:29])([CH3:28])[CH2:22][N:23]3[CH2:24][C:25]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:26])=[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 8083Morpholine

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 60043385(S)-6,6-Dimethyl-4-(2-morpholin-4-yl-2-oxo-ethyl)-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 86%

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 morpholine in 86% yield. 1H-NMR (300 MHz, DMSO-d6): δ 1.17 (s,3H), 1.30 (s,3H), 2.19 (d,1H), 2.71 (d,1H), 3.03 (d,1H), 3.16 (d,1H), 3.22 (dd,1H), 3.45-3.72 (m,7H), 3.80-3.98 (m, 3H), 7.94 (d,1H), 8.15 (d,1H), 8.21 (d,1H), 8.37 (d,1H), 9.03 (s,1H), 10.35 (s,1H), 11.28 (s,1H). Retention Time (LC, method: ammonium acetate standard): 1.56 min. MS (M+H+): 486.3.

Workup

custom1.56 min

Sources & evidence

ORD record: ord-ffcdf111c2a24608ad0437b12228abf5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951801B2

Reaction notes

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