Cyclohexanol → Cyclohexyl 2-(4-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)-1,3-thiazole-4-carboxylate

HRID 1888100Notes

Reaction equation

HRID 1888100 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C1C=CC=CN=1)C.C(N=C=NCCCN(C)C)C.[CH3:28][C:29]1[N:33]([CH2:34][C:35]([N:37]2[CH2:42][CH2:41][N:40]([C:43]3[S:44][CH:45]=[C:46]([C:48](O)=[O:49])[N:47]=3)[CH2:39][CH2:38]2)=[O:36])[N:32]=[C:31]([C:51]([F:54])([F:53])[F:52])[CH:30]=1>ClCCl.O>[CH3:28][C:29]1[N:33]([CH2:34][C:35]([N:37]2[CH2:38][CH2:39][N:40]([C:43]3[S:44][CH:45]=[C:46]([C:48]([O:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[O:49])[N:47]=3)[CH2:41][CH2:42]2)=[O:36])[N:32]=[C:31]([C:51]([F:54])([F:52])[F:53])[CH:30]=1

Participants

7

Reactant 4

HCID 7966CyclohexanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 671510882-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylic acid

Product 1

HCID 52920340Cyclohexyl 2-(4-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature, cyclohexanol (82 mg), dimethylaminopyridine (10 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (150 mg) are added to a solution of 2-(4-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)-1,3-thiazole-4-carboxylic acid (XXXIV-1, 300 mg) in dichloromethane (5 ml). The mixture is stirred overnight, and water is then added. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried with sodium sulphate. The solid is filtered off and the solvent is removed by distillation. The residue is purified chromatographically. This gives cyclohexyl 2-(4-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperazin-1-yl)-1,3-thiazole-4-carboxylate (45 mg, 12%).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. filtrationThe solid is filtered off
  5. customthe solvent is removed by distillation
  6. customThe residue is purified chromatographically

Sources & evidence

ORD record
ord-d5f56263ca1144fcbccf5900e9fbf50d
Source dataset
uspto-grants-2013_08
Patent number
US08501781B2

Reaction notes

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