1-(2-(Dimethylamino)ethyl)-5-oxopyrrolidine-3-carboxylic acid → 1-(2-dimethylamino-ethyl)-5-oxo-pyrrolidine-3-carboxylic acid (6-chloro-7-methoxy-9H-beta-carbolin-8-yl)-amide

HRID 552197

Reaction equation

HRID 552197 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:17])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:18][N:19]([CH3:31])[CH2:20][CH2:21][N:22]1[C:26](=[O:27])[CH2:25][CH:24]([C:28](O)=[O:29])[CH2:23]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:17][C:28]([CH:24]3[CH2:25][C:26](=[O:27])[N:22]([CH2:21][CH2:20][N:19]([CH3:31])[CH3:18])[CH2:23]3)=[O:29])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

3

Reactant 2

HCID 6545211-(2-(Dimethylamino)ethyl)-5-oxopyrrolidine-3-carboxylic acidHCID 213627436-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amine

Product 1

HCID 112703531-(2-dimethylamino-ethyl)-5-oxo-pyrrolidine-3-carboxylic acid (6-chloro-7-methoxy-9H-beta-carbolin-8-yl)-amideYield 60%

Procedure

Prepared according to Method A from 6-chloro-7-methoxy-9H-β-carboline-8-ylamine and 1-(2-dimethylamino-ethyl)-5-oxo-pyrrolidine-3-carboxylic acid in 60% yield following purification using a semi-preparative Chiralcel OD column with 85/7.5/7.5 hexane/EtOH/MeOH as the eluant. 1H-NMR (300 MHz, DMSO-d6): δ 2.44 (s, 6H), 2.75 (t, 2H), 2.88 (d, 2H), 3.56 (t, 2H), 3.66 (m, 1H), 3.85 (m, 2H), 3.90 (s, 3H), 8.03 (d, 1H), 8.21 (s, 1H), 8.28 (d,1H), 8.79 (s,1H). Retention Time (LC, method: ammonium acetate standard): 1.42 min. MS (M+H+): 430.

Workup

  1. customPrepared
  2. custompurification
  3. custom1.42 min

Sources & evidence

ORD record
ord-1885f67f08e044f499f82fa9fd7195b7
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Linked notes

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