Cyclohexene oxide → N-(6-{4-[4-((1S,2S)-2-hydroxy-cyclohexyl)piperazine-1-carbonyl]phenoxy}pyridin-3-yl)-4-trifluoromethylbenzamide

HRID 884174Notes

Reaction equation

HRID 884174 reaction equation
[N:1]1([C:7]([C:9]2[CH:34]=[CH:33][C:12]([O:13][C:14]3[N:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:35]1[CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH:36]12>CO>[OH:35][C@H:36]1[CH2:41][CH2:40][CH2:39][CH2:38][C@@H:37]1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[N:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:33][CH:34]=2)=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 68522218N-{6-[4-(piperazine-1-carbonyl)phenoxy]-pyridin-3-yl}-4-trifluoromethylbenzamide

Product 1

HCID 68527025N-(6-{4-[4-((1S,2S)-2-hydroxy-cyclohexyl)piperazine-1-carbonyl]phenoxy}pyridin-3-yl)-4-trifluoromethylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-{6-[4-(piperazine-1-carbonyl)phenoxy]-pyridin-3-yl}-4-trifluoromethyl-benzamide (430 mg, 0.91 mmol) in methanol was added 1,2-epoxycyclohexane (180 mg, 1.83 mmol), and the resulting solution was stirred for 1 day under reflux. The resulting reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=35:1), and then ethyl acetate was added. The precipitated white powder was filtered off and washed with ethyl acetate, to thereby yield 284 mg of the title compound.

Workup

  1. temperatureunder reflux
  2. customThe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=35:1)
  5. additionethyl acetate was added
  6. filtrationThe precipitated white powder was filtered off
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-09478e635b8145b9bcc32c7a444067bd
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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