Cyclopentanecarbonyl chloride → HCID 57883542, compound

HRID 2263805Notes

Reaction equation

Cl.[CH3:2][N:3]([CH3:36])[S:4]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[S:18][C:17]([NH:19][C:20]([N:22]([CH:29]3[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]3)[CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[O:21])=[N:16][CH:15]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5].[CH:37]1([C:42](Cl)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH3:2][N:3]([CH3:36])[S:4]([N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[S:18][C:17]([NH:19][C:20]([N:22]([CH:23]3[CH2:28][CH2:27][N:26]([C:42]([CH:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[O:43])[CH2:25][CH2:24]3)[CH:29]3[CH2:30][CH2:31][CH:32]([CH3:35])[CH2:33][CH2:34]3)=[O:21])=[N:16][CH:15]=2)[CH2:11][CH2:12]1)(=[O:5])=[O:6]

Participants

Reactant 2

HCID 78284Cyclopentanecarbonyl chloride

HCID 86611205HCID 86611205, compound

Product 1

HCID 57883542HCID 57883542, compoundYield 49.2%

Procedure

Prepared as described in general procedure (N) using 4-{2-[3-(4-methyl-cyclohexyl)-3-piperidin-4-yl-ureido]-thiazol-5-ylmethyl}-piperazine-1-sulfonic acid dimethylamide hydrochloride (50 mg, 0.088 mmol), TEA (31 μL, 0.22 mmol) and cyclopentane carbonyl chloride (13 μL, 0.11 mmol) to afford 27 mg (49%) of the desired product after purification.

Workup

customPrepared

Sources & evidence

ORD record: ord-4a6c3647a5dd44c6a273651328847ac1
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851636B2

Reaction notes

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