Water → N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)cyclopentane carboxamide

HRID 490234

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9]([CH3:12])(=O)=O)[N:3]=1.SC1[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][C:12]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)=[O:22])=[CH:16][CH:15]=2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4,6-dichloro-2-(methylsulfonyl)pyrimidine (1.96 g, 8.69 mmol) and N-(4-mercaptophenyl)cyclopentanecarboxamide (2.06 g, 8.69 mmol) in acetonitrile (40 ml) was cooled to 0° C. Triethylamine (0.88 g, 8.69 mmol, 1.21 ml) was added dropwise and the solution stirred for 10 mins at 0° C. for 10 mins and then at room temperature for 2 hrs. Water (15 ml) was added and the suspension filtered, washing with water (30 ml), and then dried to give the title compound as a pale yellow solid (1.87 g, 49%). 1H NMR (DMSO-d6) 1.50-1.61 (2H, m), 1.65-1.78 (4H, m), 1.82-1.93 (2H, m), 2.76-1.82 (1H, m), 7.52 (2H, d), 1.70-1.75 (3H, m), 10.08 (1H, s). ES+ 368.

Workup

waitat room temperature for 2 hrs
filtrationthe suspension filtered
washwashing with water (30 ml)
customdried

Sources & evidence

ORD record: ord-92fa5c76640e41d580f80adf9b9ca21a
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528142B2

Linked notes

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