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

HRID 2220243Notes

Reaction equation

HRID 2220243 reaction equation
FC1C=C(C(C)(C)CC(O)(C(F)(F)F)C=O)C2OCCC=2C=1.[F:23][C:24]1[CH:25]=[C:26]([C:33]([CH3:55])([CH3:54])[CH2:34][C:35]([OH:53])([C:49]([F:52])([F:51])[F:50])[CH:36]=[N:37][C:38]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:39]=2[CH:40]=[CH:41][NH:42][C:43]3=[O:48])[C:27]2[O:31][CH2:30][CH2:29][C:28]=2[CH:32]=1.[BH4-].[Na+]>>[F:23][C:24]1[CH:25]=[C:26]([C:33]([CH3:55])([CH3:54])[CH2:34][C:35]([OH:53])([C:49]([F:51])([F:50])[F:52])[CH2:36][NH:37][C:38]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:39]=2[CH:40]=[CH:41][NH:42][C:43]3=[O:48])[C:27]2[O:31][CH2:30][CH2:29][C:28]=2[CH:32]=1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanalHCID 68854284HCID 68854284, compound

Product 1

HCID 115763075-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]isoquinol-1(2H)-one

Procedure

Analogously to Example 1, 4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal is converted with 5-aminoisoquinol-2(1H)-one into 5-[4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]isoquinol-1(2H)-one, which is reduced with sodium borohydride to the product.

Sources & evidence

ORD record
ord-61be8c5605a24bef9a2b90ca1d35f956
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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