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Tert-butyl (2S)-4-{4-[({4-[(4-chlorophenyl)sulfonyl]cyclohexyl}carbonyl)(methyl)amino]-2-methylbenzyl}-2-methylpiperazine-1-carboxylate → 4-[(4-Chlorophenyl)sulfonyl]-N-methyl-N-(3-methyl-4-{[(3S)-3-methylpiperazin-1-yl]methyl}phenyl)cyclohexanecarboxamide

HRID 2170290
Notes
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Reaction equation

HRID 2170290 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][CH:14]([C:17]([N:19]([CH3:42])[C:20]3[CH:40]=[CH:39][C:23]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[C:22]([CH3:41])[CH:21]=3)=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][CH:14]([C:17]([N:19]([CH3:42])[C:20]3[CH:40]=[CH:39][C:23]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[C:22]([CH3:41])[CH:21]=3)=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 86700730Tert-butyl (2S)-4-{4-[({4-[(4-chlorophenyl)sulfonyl]cyclohexyl}carbonyl)(methyl)amino]-2-methylbenzyl}-2-methylpiperazine-1-carboxylate2×

Product 1

HCID 867007314-[(4-Chlorophenyl)sulfonyl]-N-methyl-N-(3-methyl-4-{[(3S)-3-methylpiperazin-1-yl]methyl}phenyl)cyclohexanecarboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 6422
Trifluoroacetic acid
Solvent

Procedure

To a solution of tert-butyl (2S)-4-{4-[({4-[(4-chlorophenyl)sulfonyl]cyclohexyl}carbonyl)(methyl)amino]-2-methylbenzyl}-2-methylpiperazine-1-carboxylate (80.2 mg, 0.13 mmol) synthesized in (10D) in dichloromethane (1 mL), trifluoroacetic acid (10 mL) was added at room temperature, and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, and the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=100:0 to 90:10 (v/v)), whereby the title compound was obtained as an oil (50.1 mg, yield: 100%).

Workup

  1. additionwas added at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=100:0 to 90:10 (v/v)), whereby the title compound

Sources & evidence

ORD record
ord-2db375145c1a425a94bb1aad25a4346f
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051255B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes