Triethylamine → HCID 57469068, compound

HRID 1928419Notes

Reaction equation

HRID 1928419 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl.[F:16][C:17]([F:51])([F:50])[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[N:21]=[C:20]([C:34]2[CH:39]=[CH:38][N:37]=[C:36]([C:40]3[CH:41]=[C:42]([S:46](Cl)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=3)[CH:35]=2)[N:19]=1>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:46]([C:42]2[CH:41]=[C:40]([C:36]3[CH:35]=[C:34]([C:20]4[N:19]=[C:18]([C:17]([F:16])([F:50])[F:51])[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=5)[N:21]=4)[CH:39]=[CH:38][N:37]=3)[CH:45]=[CH:44][CH:43]=2)(=[O:47])=[O:48])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 60209344HCID 60209344, compound

Product 1

HCID 57469068HCID 57469068, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (ice-water bath) and stirred mixture of N-methyl-piperazine (0.09 g, 0.9 mmol), triethylamine (0.09 ml, 0.63 mmol) and THF (2 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) (0.20 g, 0.34 mmol) in THF (3 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/hexane) and crystallization (dichloromethane/hexane) yielded the title compound as a white solid (0.18 g, 88%). MS (ISP) 607.6 [(M+H)+]; mp 205° 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/hexane) and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-58e9a96cc3284c688cf17c70ff57bac8
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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