Phenethylamine → HCID 57469093, compound

HRID 1989727Notes

Reaction equation

HRID 1989727 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-5d08026ad1fa4a1f90b7f323ee9d455c
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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