N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide → N-Cyclopropyl-N-{1-[3-(4-hydroxy-cyclohexylamino)-propionyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

HRID 1428955Notes

Reaction equation

HRID 1428955 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH:25]2[CH2:27][CH2:26]2)[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[NH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]1>>[CH:25]1([N:11]([CH:8]2[CH2:7][CH2:6][N:5]([C:1](=[O:4])[CH2:2][CH2:3][NH:28][CH:29]3[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]3)[CH2:10][CH2:9]2)[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=2)(=[O:13])=[O:14])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 58002117N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamideHCID 178511715HCID 178511715, compound

Product 1

HCID 24860751N-Cyclopropyl-N-{1-[3-(4-hydroxy-cyclohexylamino)-propionyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

Conditions

Temperature
150 °C

Procedure

N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (1) (125 mg, 0.31 mmol), trans-4-aminocyclohexanol (357 mg, 3.1 mmol) and ETOH (2.5 ml) were mixed together in a sealed tube and heated to 150° C. with microwave equipment for 30 min. After the reaction, the reaction mixture was evaporated in vacuum and the residue was purified by column chromatography on silica gel (CHCl3/MeOH/NH3 aq.=100/10/1) to afford the desired compound as free base, which was dissolved in AcOEt (2 ml), and treated with 4N—HCl in AcOEt (2 ml) solution. The resulting mixture was concentrated in vacuo, and dried under reduced pressure for 24 hours at 60° C. to afford the title compound 3 as a HCl-salt (colorless amorphous, 141 mg, yield 82%) LC: 100%. MS: m/z=517.88, 518.51 (M+H+).

Workup

  1. customAfter the reaction
  2. customthe reaction mixture was evaporated in vacuum
  3. customthe residue was purified by column chromatography on silica gel (CHCl3/MeOH/NH3 aq.=100/10/1)

Sources & evidence

ORD record
ord-edc36912356f48e6a2cba4dc3df8e08e
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Reaction notes

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