Methylamine → HCID 57469087, compound

HRID 1928439Notes

Reaction equation

HRID 1928439 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.Cl.[F:11][C:12]([F:46])([F:45])[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:16]=[C:15]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]3[CH:36]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=3)[CH:30]=2)[N:14]=1>C1COCC1>[CH3:3][NH:5][S:41]([C:37]1[CH:38]=[CH:39][CH:40]=[C:35]([C:31]2[CH:30]=[C:29]([C:15]3[N:14]=[C:13]([C:12]([F:46])([F:45])[F:11])[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=4)[N:16]=3)[CH:34]=[CH:33][N:32]=2)[CH:36]=1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 60209344HCID 60209344, compound

Product 1

HCID 57469087HCID 57469087, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (ice-water bath) and stirred mixture of methylamine solution (2M in THF) (1.5 ml, 3.0 mmol), triethylamine (0.29 ml, 2.1 mmol) and THF (4 ml) was added drop wise a solution of 3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonyl chloride hydrochloride (example I.1) (0.58 g, 1.0 mmol) in THF (6 ml). The mixture was allowed to stir at room temperature for 16 h. Purification of the reaction mixture by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/MeOH/hexane) yielded the title compound as a white solid (0.46 g, 92%). MS (ISP) 538.8 [(M+H)+]; mp 174° C.

Workup

  1. stirringto stir at room temperature for 16 h
  2. customPurification of the reaction mixture by flash chromatography
  3. customon silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-130c1a62f9e04933bbaf489cb7e0eb1a
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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