Cyclobutylamine → HCID 57917682, compound

HRID 1878395Notes

Reaction equation

HRID 1878395 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][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:10]([CH3:29])([CH3:28])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:32].Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[CH:46]1([NH2:50])[CH2:49][CH2:48][CH2:47]1>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:30]=[CH:31][C:2]([NH:1][C:34]([NH:50][CH:46]4[CH2:49][CH2:48][CH2:47]4)=[O:35])=[C:3]([F:32])[CH:4]=3)[CH2:9][C:10]2([CH3:29])[CH3:28])[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 821294-Nitrophenyl chloroformateHCID 57917599HCID 57917599, compound

Product 1

HCID 57917682HCID 57917682, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-((4-(4-amino-3-fluorobenzoyl)-2,2-dimethylpiperazin-1-yl)methyl)-N-tert-butylbenzamide (0.1 mmol, 45 mg) in dichloromethane (1.5 mL) was added 4-nitrophenyl chloroformate (0.11 mmol, 23 mg). The mixture was allowed to stir for 2 hours before the addition of cyclobutylamine (1.757 mmol, 125 mg, 150 μl). The mixture was allowed to stir for a further 16 hours before being concentrated under vacuum and purified by acidic reverse phase HPLC. The free base of the product was obtained using strong cation exchange column chromatography. This material was lyophilised to yield the title compound (16 mg).

Workup

  1. concentrationbefore being concentrated under vacuum
  2. custompurified by acidic reverse phase HPLC
  3. customThe free base of the product was obtained

Sources & evidence

ORD record
ord-4955a4a629734803982e719124a9a179
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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