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

HRID 1746775Notes

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][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:35][CH2:34]1>C(O)C>[CH:38]1([N:37]([CH2:36][CH:33]2[CH2:34][CH2:35]2)[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)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]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)cyclohexanamine (54.4 mg; 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 (110 mg, 84%).

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-94868dfe55ed44e29d4a03c3b6f1d15f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

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