Triethylamine → 4,6-Dichloro-N-(4-(N-methylsulfamoyl)phenyl)pyrimidine-5-carboxamide

HRID 1052556Notes

Reaction equation

HRID 1052556 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:20][C:21]1[C:26]([C:27](Cl)=[O:28])=[C:25]([Cl:30])[N:24]=[CH:23][N:22]=1>O1CCCC1.ClCCl>[Cl:20][C:21]1[C:26]([C:27]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH:11][CH3:12])=[CH:4][CH:3]=2)=[O:28])=[C:25]([Cl:30])[N:24]=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride2×

Product 1

HCID 1184339234,6-Dichloro-N-(4-(N-methylsulfamoyl)phenyl)pyrimidine-5-carboxamideYield 50.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-N-methylbenzenesulfonamide (244 mg, 1.31 mmol) was dissolved in tetrahydrofuran (12 ml) and triethylamine (402 μl, 2.88 mmol) was added. Then a solution of 4,6-dichloropyrimidine-5-carbonyl chloride (300 mg, 1.42 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dropwise added. After 2 h more triethylamine (202 μl, 1.44 mmol) and 4,6-dichloropyrimidine-5-carbonyl chloride (150 mg, 0.71 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. The crude was purified by flash chromatography (0% to 60%, hexane-ethyl acetate) using a SP1® Purification System to give 238 mg (50% yield) of the title compound. Purity 100%.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography (0% to 60%, hexane-ethyl acetate)
  6. customa SP1® Purification System

Sources & evidence

ORD record
ord-4d95eeaf02544a8fbe59b2344e44e24c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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