Cyclopropylamine → HCID 23130587, compound

HRID 2080178Notes

Reaction equation

HRID 2080178 reaction equation
[NH2:1][C:2]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[O:5].[CH:27]1([NH2:30])[CH2:29][CH2:28]1>O1CCCC1>[NH2:1][C:2]1[N:25]=[C:24]([NH:30][CH:27]2[CH2:29][CH2:28]2)[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[O:5]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 231305612-Amino-6-chloro-N-(4-benzyloxy-benzyl)-nicotinamide

Product 1

HCID 23130587HCID 23130587, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

2-Amino-6-chloro-N-(4-benzyloxy-benzyl)-nicotinamide described in Example A-27 (80 mg, 0.22 mmol) was dissolved in tetrahydrofuran (3 mL), cyclopropylamine (0.3 mL, 4.3 mmol) was added thereto, and the solution was heated in a sealed tube for 16 hours (oil bath temperature: 140° C.). The reaction solution was allowed to room temperature, the solution was concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1), and the title compound (12 mg, 0.031 mmol, 14%) was obtained.

Workup

  1. customwas allowed to room temperature
  2. concentrationthe solution was concentrated
  3. customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-896933e92c7d4c03b9e2b3bbe1ad4dbf
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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