3,3-Dimethylbutylamine → 6-{4-[(3,3-Dimethyl-butylamino)-methyl]-2-fluoro-6-methoxy-phenoxy}-nicotinamide

HRID 130962Notes

Reaction equation

HRID 130962 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[C:14]([O:20][CH3:21])[C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1.[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH2:25][NH2:26].[BH4-].[Na+]>>[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH2:25][NH:26][CH2:18][C:16]1[CH:15]=[C:14]([O:20][CH3:21])[C:3]([O:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=2)=[C:2]([F:1])[CH:17]=1

Participants

4

Reactant 3

HCID 197093,3-DimethylbutylamineHCID 4311764Sodium borohydrideHCID 597302826-(2-Fluoro-4-formyl-6-methoxy-phenoxy)-nicotinamide

Product 1

HCID 100908706-{4-[(3,3-Dimethyl-butylamino)-methyl]-2-fluoro-6-methoxy-phenoxy}-nicotinamideYield 80.1%

Procedure

Using a method similar to Example 710, Step 4, using 6-(2-fluoro-4-formyl-6-methoxy-phenoxy)-nicotinamide (250 mg, 0.861 mmol), 3,3-dimethyl-butylamine (104 mg, 1.03 mmol), and NaBH4 (49 mg, 1.29 mmol) gave the title compound (259 mg) as a white solid. Mass spectrum (ion spray): m/z=376 (M+1);

Sources & evidence

ORD record
ord-00b4ff6bcc94484ba222c06967cefd64
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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