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

HRID 229430Notes

Reaction equation

HRID 229430 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.[F:23][C:24]([F:37])([F:36])[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>>[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]([C:24]([F:23])([F:36])[F:37])=[CH:26][CH:27]=3)[CH2:31][CH2:32]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

Participants

3

Reactant 2

HCID 138976418-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-oneHCID 231061381-(4-Trifluoromethylbenzyl)cyclopropylamine

Product 1

HCID 231061178-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Procedure

Reaction of 587 mg (2.0 mmol) 8-benzyloxy-5-oxiranyl-1H-quinolin-2-one and 710 mg (3.3 mmol) 1-(4-trifluoromethyl-benzyl)-cyclopropylamine is carried out analogously to Example 40a43a). Yield: 322 mg (32%); mass spectroscopy: [M+H]+=509.

Sources & evidence

ORD record
ord-b469873639ab49739dc7bc4029f13445
Source dataset
uspto-grants-2009_07
Patent number
US07563806B2

Reaction notes

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