Phenethylamine → HCID 57469093, compound

HRID 1928446Notes

Reaction equation

HRID 1928446 reaction equation
C(N)[CH2:2][C:3]1[CH:8]=CC=CC=1.C([N:12](CC)CC)C.Cl.[F:18][C:19]([F:53])([F:52])[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[N:23]=[C:22]([C:36]2[CH:41]=[CH:40][N:39]=[C:38]([C:42]3[CH:43]=[C:44]([S:48](Cl)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=3)[CH:37]=2)[N:21]=1>C1COCC1>[CH:3]1([NH:12][S:48]([C:44]2[CH:45]=[CH:46][CH:47]=[C:42]([C:38]3[CH:37]=[C:36]([C:22]4[N:21]=[C:20]([C:19]([F:53])([F:52])[F:18])[CH:25]=[C:24]([C:26]5[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=5)[N:23]=4)[CH:41]=[CH:40][N:39]=3)[CH:43]=2)(=[O:50])=[O:49])[CH2:2][CH2:8]1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 60209344HCID 60209344, compound

Product 1

HCID 57469093HCID 57469093, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (ice-water bath) and stirred mixture of phenethylamine (0.165 g, 3.0 mmol), triethylamine (0.28 ml, 2.0 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) (0.56 g, 0.96 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 (0.49 g, 96%). MS (ISP) 564.7 [(M+H)+]; mp 195.5° 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-20e5949ddee34f37ba3563aee0fb9fab
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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