Cyclopropanemethanamine → HCID 57917614, compound

HRID 1878439Notes

Reaction equation

HRID 1878439 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:28]=[CH:29][CH:30]=3)[C:18]([NH:20][C:21]([C:26]#[N:27])([CH:23]3[CH2:25][CH2:24]3)[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:33].C1C([N+]([O-])=O)=CC=C([Cl-][C:44]([O-])=[O:45])C=1.[CH:47]1([CH2:50][NH2:51])[CH2:49][CH2:48]1>ClCCl>[C:26]([C:21]([NH:20][C:18](=[O:19])[C:17]1[CH:28]=[CH:29][CH:30]=[C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]3[CH:31]=[CH:32][C:2]([NH:1][C:44]([NH:51][CH2:50][CH:47]4[CH2:49][CH2:48]4)=[O:45])=[C:3]([F:33])[CH:4]=3)[CH2:13][CH2:12]2)[CH:16]=1)([CH:23]1[CH2:25][CH2:24]1)[CH3:22])#[N:27]

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 579176753-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamide

Product 1

HCID 57917614HCID 57917614, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)—N-(1-cyano-1-cyclopropyl-ethyl)benzamide (49 mg, 0.109 mmol) was stirred In dichloromethane at room temperature. 4-Nitrophenylchloroformate (22 mg, 0.109 mmol) was added and the reaction mixture stirred for 30 minutes. Cyclopropylmethylamine (23 mg, 0.327 mmol) was added and the reaction allowed to stir for 30 minutes at room temperature. The reaction was concentrated under reduced pressure and the resulting residue purified by silica column chromatography to afford the title compound (25 mg). MS (ESI) m/z 547.5 [M+H]+

Workup

  1. stirringto stir for 30 minutes at room temperature
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe resulting residue purified by silica column chromatography

Sources & evidence

ORD record
ord-1603cbe733c74f4fbe0ec3929d9fa2fa
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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