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

HRID 1746741Notes

Reaction equation

HRID 1746741 reaction equation
[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][C:18]=3[CH3:27])=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][NH:33][CH3:34]>C1COCC1>[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([N:33]([CH3:34])[CH3:32])(=[O:25])=[O:24])=[CH:19][C:18]=3[CH3:27])=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 594468814-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride2×

Product 1

HCID 251829116-[cyclohexyl(cyclopropylmethyl)amino]-N-{4-[(dimethylamino)sulfonyl]-2-methylphenyl}pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride (Intermediate 20, 50 mg; 0.11 mmol) in THF (5 ml) was treated with polymer-supported-diisopropylethylamine (60.7 mg; 0.22 mmol) and dimethylamine (8 μl; 0.13 mmol, Aldrich) and the reaction mixture was stirred at room temperature for three hours. The resin was filtered and the solvents were evaporated to give a residue, which was purified by column chromatography (silica) using as eluent petroleum ether/EtOAc to afford the title compound as a yellow oil.

Workup

  1. filtrationThe resin was filtered
  2. customthe solvents were evaporated
  3. customto give a residue, which
  4. customwas purified by column chromatography (silica)

Sources & evidence

ORD record
ord-57103ae2b93d44b4b75e8018ce1a6cb5
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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