Methylamine → HCID 57469087, compound

HRID 1989720Notes

Reaction equation

HRID 1989720 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 1.1) (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-cbfe72896ad7440db60522b6cbe3521a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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