Isoamylamine → 6-{2,6-Difluoro-4-[(3-methyl-butylamino)-methyl]-phenoxy}-nicotinamide

HRID 228420Notes

Reaction equation

HRID 228420 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[C:14]([F:20])[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.[CH2:21]([NH2:26])[CH2:22][CH:23]([CH3:25])[CH3:24].[BH4-].[Na+]>>[F:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:26][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:15]=[C:14]([F:20])[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

Participants

4

Reactant 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 597299106-(2,6-Difluoro-4-formyl-phenoxy)-nicotinamide

Product 1

HCID 100891626-{2,6-Difluoro-4-[(3-methyl-butylamino)-methyl]-phenoxy}-nicotinamideYield 84.7%

Procedure

Using a method similar to Example 712, using 6-(2,6-difluoro-4-formyl-phenoxy)-nicotinamide (Example 712, Step 1) (139 mg, 0.500 mmol), isoamylamine (52 mg, 0.600 mmol), and NaBH4 (28 mg, 0.750 mmol) gave the title compound (148 mg) as a white solid. Mass spectrum (ion spray): m/z=350 (M+1); 1HNMR (CDCl3): 8.51 (s, 1H), 8.21 (d, 1H), 7.14 (d, 1H), 7.03 (d, 2H), 5.74 (br. s, 9H), 3.79 (s, 2H), 2.65 (t, 2H), 1.66 (m, 1H), 1.41 (m, 2H), 0.91 (d, 6H).

Sources & evidence

ORD record
ord-af9c826ec32b49abbb089f86ee1fce82
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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