Ammonium Acetate → 1,2,2-trimethyl-5-oxo-pyrrolidine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552184Notes

Reaction equation

HRID 552184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:16][N:17]1[C:21](=[O:22])[CH2:20][CH:19]([C:23](O)=[O:24])[C:18]1([CH3:27])[CH3:26].C([O-])(=O)C.[NH4+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:23]([CH:19]3[CH2:20][C:21](=[O:22])[N:17]([CH3:16])[C:18]3([CH3:27])[CH3:26])=[O:24])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 213627016-Chloro-9H-beta-carbolin-8-amineHCID 567377631,2,2-Trimethyl-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 114515461,2,2-trimethyl-5-oxo-pyrrolidine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 68%

Procedure

The desired compound was prepared according to Method B from 6-chloro-9H-β-carboline-8-ylamine and 1,2,2-trimethyl-5-oxo-pyrrolidine-3-carboxylic acid in 68% yield. 1H-NMR (DMSO-d6, 300 MHz) δ 1.23 (s, 3H), 1.45 (s, 3H), 2.59 (dd, 1H), 2.66(s, 3H), 2.70 (dd, 1H), 3.17 (t, 1H), 7.91 (m, 1H), 8.18 (d, 1H), 8.24 (d, 1H), 8.40 (d, 1H), 9.07 (s, 1H), 10.16 (s, 1H), 11.32 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.17 min. MS (M+H+): 371.3.

Workup

  1. custom1.17 min

Sources & evidence

ORD record
ord-8971a0828f544af780491cb5656fc91c
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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