Methylamine → 6-chloro-N-(2-methyl-4-(N-methylsulfamoyl)phenyl)pyrimidine-4-carboxamide

HRID 1746678Notes

Reaction equation

HRID 1746678 reaction equation
[Cl:1][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](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1.CN.[CH:24]([NH:27]C(C)C)(C)C>C1COCC1>[Cl:1][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:19])(=[O:18])[NH:27][CH3:24])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7912DiisopropylamineHCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride2×

Product 1

HCID 594468616-chloro-N-(2-methyl-4-(N-methylsulfamoyl)phenyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 400 mg; 1.15 mmol) in THF (20 ml) was treated with methylamine (0.7 ml, 2M in THF; 1.4 mmol) and diisopropylamine (0.4 ml; 2.9 mmol). After stirring at RT for 18 hours the solvent was removed in vacuo and the residue redissolved in DCM and washed with water. The organic extracts were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc. The title product was obtained as a white solid.

Workup

  1. customwas removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (silica)
  6. washeluting with petroleum ether containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-0a62b9bc1fa3454b85f4f55cfa4ddb37
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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