Sodium cyanoborohydride → 5-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-2,6-dimethylquinoline

HRID 2220244Notes

Reaction equation

HRID 2220244 reaction equation
FC1C=C(C(C)(C)CC(O)(C(F)(F)F)C=O)C2OCCC=2C=1.NC1C(C)=CC=C2C=1C=CC(C)=N2.[F:36][C:37]1[CH:38]=[C:39]([C:46]([CH3:69])([CH3:68])[CH2:47][C:48]([OH:67])([C:63]([F:66])([F:65])[F:64])[CH:49]=[N:50][C:51]2[C:60]([CH3:61])=[CH:59][CH:58]=[C:57]3[C:52]=2[CH:53]=[CH:54][C:55]([CH3:62])=[N:56]3)[C:40]2[O:44][CH2:43][CH2:42][C:41]=2[CH:45]=1.C([BH3-])#N.[Na+]>>[F:36][C:37]1[CH:38]=[C:39]([C:46]([CH3:69])([CH3:68])[CH2:47][C:48]([OH:67])([C:63]([F:64])([F:66])[F:65])[CH2:49][NH:50][C:51]2[C:60]([CH3:61])=[CH:59][CH:58]=[C:57]3[C:52]=2[CH:53]=[CH:54][C:55]([CH3:62])=[N:56]3)[C:40]2[O:44][CH2:43][CH2:42][C:41]=2[CH:45]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 50336872,6-Dimethylquinolin-5-amineHCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanalHCID 688558355-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2,6-dimethylquinoline

Product 1

HCID 115619785-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-2,6-dimethylquinoline

Procedure

Analogously to Example 1, 4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal is converted with 5-amino-2,6-dimethylquinoline into 5-[4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2,6-dimethylquinoline, which is reduced with sodium cyanoborohydride to the product.

Sources & evidence

ORD record
ord-edc2a7c205424dbc9ee444705fcbebcd
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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