2,6-Dimethylmorpholine → (3S)-N-(6-Chloro-9H-pyrido[3,4-b]indol-8-yl)-4-[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-2-oxoethyl]-6,6-dimethyl-3-morpholinecarboxamide

HRID 552251Notes

Reaction equation

HRID 552251 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH: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.[CH3:30][CH:31]1[O:36][CH:35]([CH3:37])[CH2:34][NH:33][CH2:32]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH:18]3[CH2:19][O:20][C:21]([CH3:29])([CH3:28])[CH2:22][N:23]3[CH2:24][C:25]([N:33]3[CH2:32][CH:31]([CH3:30])[O:36][CH:35]([CH3:37])[CH2:34]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

3

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 59337527[5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid

Product 1

HCID 67165125(3S)-N-(6-Chloro-9H-pyrido[3,4-b]indol-8-yl)-4-[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-2-oxoethyl]-6,6-dimethyl-3-morpholinecarboxamide

Procedure

The desired compound was prepared using [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 2,6-dimethyl morpholine following Method F. Chromatographic purification gave the desired product in 70-80% yield. 1H-NMR (300 MHz, CDCl3): δ 9.31 (s, 1H), 8.75 (d, 1H), 8.55 (d, 1H), 8.37 (d, 1H), 8.14 (m, 1H), 4.73 (m, 2H), 4.96 (m, 1H), 4.37 (m, 2H), 3.69 (m, 2H), 3.57 (m, 4H), 2.82 (t, 1H), 2.47 (t, 1H), 1.50 (d, 3H), 1.42 (d, 3H), 1.18 (m, 6H). Retention Time (LC, method: formic acid standard): 1.14 min (Diode Array).

Workup

  1. customThe desired compound was prepared
  2. customChromatographic purification

Sources & evidence

ORD record
ord-3727c8efaf2842c4ab16fbe3ca961f09
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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