Diisopropylamine → 6-[(cyclopropylmethyl)(propyl)amino]-N-(4-{[(2-methoxyethyl)amino]sulfonyl}-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946794Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 6-chloro-N-(4-(N-(2-methoxyethyl)sulfamoyl)-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 38, 100 mg; 0.26 mmol) and diisopropylamine (91 mL; 0.52 mmol) in ethanol (2.5 ml) was treated with N-(cyclopropylmethyl)propan-1-amine (0.7 ml, 0.33 mmol). The mixture was heated to 160° C. in a microwave for 1 hour and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid.

Workup

customthe solvent removed in vacuo
customThe residue was purified by column chromatography (silica)
washeluting with petroleum ether containing
temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record: ord-069c67f6c9ac47dabeea514ba231cdf0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399448B2

Reaction notes

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