1-Ethylpiperazin-2-one → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-ethyl-3-oxopiperazin-1-yl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879618Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH2:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][C:38]1=[O:43])[CH3:36]>CN(C=O)C>[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:40]4[CH2:41][CH2:42][N:37]([CH2:35][CH3:36])[C:38](=[O:43])[CH2:39]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (15.0 mg, 0.029 mmol) in DMF (0.4 mL) was added 1-ethylpiperazin-2-one (7.4 mg, 0.058 mmol). The reaction mixture was heated at 100° C. overnight. Reaction mixture was concentrated in vacuo and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the product. LCMS-ESI+: calc'd for C31H35ClN5O4S: 608.2 (M+H+); Found: 608.2 (M+H+).

Workup

customReaction mixture
concentrationwas concentrated in vacuo
custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)
customto give the product

Sources & evidence

ORD record: ord-50d4ed822ada4d6f8666ef194627dfe0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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