Cyclobutylamine → HCID 25191378, compound

HRID 1878339Notes

Reaction equation

HRID 1878339 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][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])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[Cl:30].C1C([N+]([O-])=O)=CC=C([Cl-][C:41]([O-])=[O:42])C=1.[CH:44]1([NH2:48])[CH2:47][CH2:46][CH2:45]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:28]=[CH:29][C:2]([NH:1][C:41]([NH:48][CH:44]4[CH2:47][CH2:46][CH2:45]4)=[O:42])=[C:3]([Cl:30])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 57917645HCID 57917645, compound

Product 1

HCID 25191378HCID 25191378, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (200 mg, 0.466 mmol) and 4-nitrophenylchloroformate (94 mg, 0.466 mmol) were heated to reflux in dichloromethane (10 ml) for 2 hours. Cyclobutylamine (99 mg, 1.398 mmol) was added and the reaction stirred overnight. The reaction mixture was washed with water, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by acidic reverse phase HPLC to afford the title compound (20 mg).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe resulting residue was purified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-7538ca93e9a34138903f86fdd976cd92
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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