Isobutylamine → (S)-N-tert-Butyl-3-((4-(3-fluoro-4-(3-isobutylureido)benzoyl)-2-isopropylpiperazin-1-yl)methyl)benzamide

HRID 1878388Notes

Reaction equation

HRID 1878388 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:10]([CH:28]([CH3:30])[CH3:29])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:33].Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].[CH2:47]([NH2:51])[CH:48]([CH3:50])[CH3:49]>ClCCl>[C:21]([NH:20][C:18](=[O:19])[C:17]1[CH:25]=[CH:26][CH:27]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:31]=[CH:32][C:2]([NH:1][C:35]([NH:51][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:36])=[C:3]([F:33])[CH:4]=3)[CH2:9][C@@H:10]2[CH:28]([CH3:29])[CH3:30])[CH:16]=1)([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 821294-Nitrophenyl chloroformateHCID 57917701HCID 57917701, compound

Product 1

HCID 57917694(S)-N-tert-Butyl-3-((4-(3-fluoro-4-(3-isobutylureido)benzoyl)-2-isopropylpiperazin-1-yl)methyl)benzamideYield 6.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-3-((4-(4-amino-3-fluorobenzoyl)-2-isopropylpiperazin-1-yl)methyl)-N-tert-butylbenzamide (40 mg, 0.088 mmol) in dichloromethane (2 mL) at room temperature was added 4-nitrophenyl chloroformate (18.62 mg, 0.092 mmol). The reaction mixture was stirred for 1 hour before the addition of isobutylamine (6.44 mg, 0.088 mmol). After 2 hours stirring, the reaction mixture was applied to a silica carbonate column (2 g). The eluant was concentrated under vacuum and redissolved in methanol. Purification by HPLC gave the title compound (3 mg). MS (ESI) m/z 554.3 [M+H]+

Workup

  1. concentrationThe eluant was concentrated under vacuum
  2. dissolutionredissolved in methanol
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-2846bd32c4eb4b0da518e5ceaacb2e64
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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