8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one → 8-benzyloxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

HRID 29851Notes

Reaction equation

HRID 29851 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]2[CH2:22][O:21]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:35]=[CH:34][C:28]([CH2:29][C:30]2([NH2:33])[CH2:32][CH2:31]2)=[CH:27][CH:26]=1>C(O)CCC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:21])[CH2:22][NH:33][C:30]2([CH2:29][C:28]3[CH:34]=[CH:35][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[CH2:32][CH2:31]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 138976418-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-oneHCID 231060921-(4-Methoxybenzyl)cyclopropanamine

Product 1

HCID 231060808-benzyloxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

587 mg (2.0 mmol) 8-benzyloxy-5-oxiranyl-1H-quinolin-2-one and 480 mg (2.7 mmol) 1-(4-methoxy-benzyl)-cyclopropylamine are refluxed in 10 mL n-butanol for 10 hours. Then the solvent is distilled off and the residue is purified by chromatography (reverse phase, water/acetonitrile gradient). Yield: 259 mg (27%); mass spectroscopy: [M+H]+=471.

Workup

  1. distillationThen the solvent is distilled off
  2. customthe residue is purified by chromatography (reverse phase, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-051b0d87bc0f41dc9d250b021bfe51f6
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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