Sodium borohydride → 5-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-1-methylisoquinoline

HRID 2220242Notes

Reaction equation

HRID 2220242 reaction equation
FC1C=C(C(C)(C)CC(O)(C(F)(F)F)C=O)C2OCCC=2C=1.NC1C=CC=C2C=1C=CN=C2C.[F:35][C:36]1[CH:37]=[C:38]([C:45]([CH3:67])([CH3:66])[CH2:46][C:47]([OH:65])([C:61]([F:64])([F:63])[F:62])[CH:48]=[N:49][C:50]2[CH:59]=[CH:58][CH:57]=[C:56]3[C:51]=2[CH:52]=[CH:53][N:54]=[C:55]3[CH3:60])[C:39]2[O:43][CH2:42][CH2:41][C:40]=2[CH:44]=1.[BH4-].[Na+]>>[F:35][C:36]1[CH:37]=[C:38]([C:45]([CH3:67])([CH3:66])[CH2:46][C:47]([OH:65])([C:61]([F:62])([F:64])[F:63])[CH2:48][NH:49][C:50]2[CH:59]=[CH:58][CH:57]=[C:56]3[C:51]=2[CH:52]=[CH:53][N:54]=[C:55]3[CH3:60])[C:39]2[O:43][CH2:42][CH2:41][C:40]=2[CH:44]=1

Participants

5

Reactant 4

HCID 4311764Sodium borohydrideHCID 99894901-Methylisoquinolin-5-amineHCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanalHCID 688538955-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-1-methylisoquinoline

Product 1

HCID 114963325-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-1-methylisoquinoline

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-1-methylisoquinoline into 5-[4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-1-methylisoquinoline, which is reduced with sodium borohydride to the product.

Sources & evidence

ORD record
ord-93911ea1fbee44e9ae29144d694c6ef4
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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