Water → Cyclohexyl 2-{1-[(2,5-difluorobenzyl)sulphonyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

HRID 1888098Notes

Reaction equation

HRID 1888098 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][S:10](Cl)(=[O:12])=[O:11].[Cl-].[CH:15]1([O:21][C:22]([C:24]2[N:25]=[C:26]([CH:29]3[CH2:34][CH2:33][NH2+:32][CH2:31][CH2:30]3)[S:27][CH:28]=2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][S:10]([N:32]1[CH2:31][CH2:30][CH:29]([C:26]2[S:27][CH:28]=[C:24]([C:22]([O:21][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:23])[N:25]=2)[CH2:34][CH2:33]1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2761456(2,5-difluorophenyl)methanesulfonyl ChlorideHCID 669115194-{4-[(Cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride

Product 1

HCID 52920339Cyclohexyl 2-{1-[(2,5-difluorobenzyl)sulphonyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, (2,5-difluorophenyl)methanesulphonyl chloride (226 mg) is added to a solution of 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride (VII-1, 330 mg) and triethylamine (303 mg) in dichloromethane (5 ml). The mixture is stirred at room temperature overnight, and water is then added. The aqueous phase is separated off and extracted with ethyl acetate, and the combined organic phases are then 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-{1-[(2,5-difluorobenzyl)sulphonyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate (156 mg, 32%).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic phases are then 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-4e7eb804dcd2430eb3ec43b8829f910e
Source dataset
uspto-grants-2013_08
Patent number
US08501781B2

Reaction notes

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