Ethanolamine → N-(2-Hydroxy-ethyl)-3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide

HRID 1928407Notes

Reaction equation

HRID 1928407 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.Cl.[F:13][C:14]([F:48])([F:47])[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[N:18]=[C:17]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([C:37]3[CH:38]=[C:39]([S:43](Cl)(=[O:45])=[O:44])[CH:40]=[CH:41][CH:42]=3)[CH:32]=2)[N:16]=1>C1COCC1>[OH:2][CH2:1][CH2:3][NH:4][S:43]([C:39]1[CH:40]=[CH:41][CH:42]=[C:37]([C:33]2[CH:32]=[C:31]([C:17]3[N:16]=[C:15]([C:14]([F:13])([F:47])[F:48])[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=4)[N:18]=3)[CH:36]=[CH:35][N:34]=2)[CH:38]=1)(=[O:44])=[O:45]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 60209344HCID 60209344, compound

Product 1

HCID 57469057N-(2-Hydroxy-ethyl)-3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (ice-water bath) and stirred mixture of ethanolamine (0.066 g, 1.08 mmol), triethylamine (0.11 ml, 0.76 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) (0.21 g, 0.36 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 (diethyl ether/hexane) yielded the title compound as a white solid (0.156 g, 76%). MS (ISP) 569.2 [(M+H)+]; mp 192.5° 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/hexane) and crystallization (diethyl ether/hexane)

Sources & evidence

ORD record
ord-fcbb34c9e66f47a8b284bd7334b1012c
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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