Sodium cyanoborohydride → 5-[4-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]quinolin-2[1H]-one

HRID 2220248Notes

Reaction equation

HRID 2220248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH:14]=O)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28](=[O:34])[NH:29]2.C([BH3-])#N.[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([OH:20])([C:16]([F:17])([F:18])[F:19])[CH2:14][NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[CH:26]=[CH:27][C:28](=[O:34])[NH:29]3)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 157190785-Amino-1,2-dihydroquinolin-2-oneHCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal

Product 1

HCID 117123825-[4-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]quinolin-2[1H]-one

Procedure

Analogously to Example 1, the corresponding imine is produced starting from 250 mg of 4-(2,3-dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal and 124 mg of 5-aminoquinolin-2[1H]-one. After reaction with sodium cyanoborohydride, the title compound is obtained.

Sources & evidence

ORD record
ord-9fd161e9957643f0aa1974677e825d2b
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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