1-Methylpiperazine → N-{5-[4-Methanesulfonyl-3-(4-methyl-piperazin-1-yl)-phenyl]-4-methyl-thiazol-2-yl}-acetamide

HRID 1092972Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CS(C)=O>[CH3:11][S:8]([C:7]1[CH:6]=[CH:5][C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])=[CH:3][C:2]=1[N:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 115 °C

Procedure

A stirred mixture of N-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 64) (0.05 g, 0.15 mmol) and 1-methylpiperazine (0.1 ml, 0.9 mmol) in dry DMSO (1 ml) is heated under argon at 115° C. for 1 hour. The solvent is removed and water (30 ml) is added. The product is extracted with ethyl acetate (2×30 ml) and the combined organic extracts are washed with brine (20 ml) and dried (MgSO4). Removal of the solvent and trituration with diethyl ether affords the title compound as a yellow solid.

Workup

customThe solvent is removed
additionwater (30 ml) is added
extractionThe product is extracted with ethyl acetate (2×30 ml)
washthe combined organic extracts are washed with brine (20 ml)
dry with materialdried (MgSO4)
customRemoval of the solvent and trituration with diethyl ether

Sources & evidence

ORD record: ord-1b1f61b2b7ae4a549658be18b29f303f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129541B2

Reaction notes

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