2-Pyrrolidone → HCID 22992247, compound

HRID 1168177Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH3:9][O:10][C:11]1[C:16]2[N:17]=[C:18]([NH:20][C:21](=[O:30])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][CH:23]=3)[S:19][C:15]=2[C:14]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:13][CH:12]=1>CN(C)C=O>[CH3:9][O:10][C:11]1[C:16]2[N:17]=[C:18]([NH:20][C:21](=[O:30])[C:22]3[CH:23]=[CH:24][C:25]([CH2:28][N:3]4[CH2:7][CH2:6][CH2:5][C:4]4=[O:8])=[CH:26][CH:27]=3)[S:19][C:15]=2[C:14]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride (48 ms, 0.48 mmol, 60% in mineral oil) are suspended in dimethyl formamide (2.0 ml) and at 0° C. treated with pyrrolidin-2-one. After stirring for 1 h at 50° C., N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4-chloromethyl-benzamide (200 mg, 0.48 mmol) was added and the solution stirred for 5 h at 80° C. Removal of the volatile components in vacuo and flash chromatography (silica, eluent dichloromethane/methanol 19:1) afforded the title compound as off-white crystals (86% yield). MS: m/e=467(M+H+).

Workup

stirringthe solution stirred for 5 h at 80° C
customRemoval of the volatile components in vacuo and flash chromatography (silica, eluent dichloromethane/methanol 19:1)

Sources & evidence

ORD record: ord-03daea6ae35943388dd954ca1e0dcfcf
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624163B2

Reaction notes

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