Acetone → HCID 59750658, compound

HRID 422248Notes

Reaction equation

HRID 422248 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([O:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)=[CH:7][CH:6]=[CH:5][C:4]1=2.[CH3:23][C:24]([CH3:26])=O.[BH3-]C#N.[Na+]>>[CH:24]([NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([O:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)=[CH:7][CH:6]=[CH:5][C:4]1=2)([CH3:26])[CH3:23]

Participants

4

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 59750691HCID 59750691, compound2×

Product 1

HCID 59750658HCID 59750658, compoundYield 41%

Procedure

Using a method similar to Example 204, using 6-S-aminomethyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-nicotinamide (intermediate 20, 297 mg, 1.00 mmol), acetone (116 mg, 2.00 mmol), and NaBH3CN (125 mg, 2.00 mmol) gives the title compound (139 mg) as a white foam. Mass spectrum (ion spray): m/z=340 (M+1); 1HNMR (CDCl3): 8.57 (s, 1H), 8.13 (d, 1H), 7.21-7.13 (m, 2H), 6.90-6.87 (m, 2H), 6.27 (br. s, 2H), 2.97 (m, 1H), 2.91-2.75 (m, 3H), 2.62-2.41 (m, 2H), 1.83-1.63 (m, 4H), 1.07 (d, 6H).

Sources & evidence

ORD record
ord-d1ce42ce265440daaf040393387228a2
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

Loading…