3-Cyclohexylpropylamine → 6-(cyclohexyl(propyl)amino)-N-(2-methyl-4-sulfamoylphenyl)pyrimidine-4-carboxamide

HRID 1746732Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([S:8](=[O:11])(=[O:10])[NH2:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1)=[O:14].[CH:22]1(CCCN)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[NH2:9][S:8]([C:6]1[CH:5]=[CH:4][C:3]([NH:12][C:13]([C:15]2[CH:20]=[C:19]([N:12]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:3][CH2:2][CH3:1])[N:18]=[CH:17][N:16]=2)=[O:14])=[C:2]([CH3:1])[CH:7]=1)(=[O:11])=[O:10]

Participants

Reactant 2

HCID 126663903-Cyclohexylpropylamine

HCID 594470566-Chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)amide2×

Product 1

HCID 251827826-(cyclohexyl(propyl)amino)-N-(2-methyl-4-sulfamoylphenyl)pyrimidine-4-carboxamideYield 82%

Procedure

Following the general method as outlined in Example 20, starting from 6-chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)-amide (Intermediate 17) and cyclohexylpropylamine (Chembridge), the title compound was obtained as a beige solid in 82% yield.

Sources & evidence

ORD record: ord-56b7a47d84e64e8c956d586e1d29c142
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

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