3,3-Dimethylbutanal → HCID 59750681, compound

HRID 422244Notes

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]([CH3:29])([CH3:28])[CH2:25][CH:26]=O.[BH4-].[Na+]>>[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][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

Participants

Reactant 3

HCID 763353,3-Dimethylbutanal

HCID 4311764Sodium borohydride

HCID 59750691HCID 59750691, compound2×

Product 1

HCID 59750681HCID 59750681, compoundYield 68.2%

Procedure

Using a method similar to Example 201, using 6-(5-aminomethyl-5,6,7,8-tetrahydro-naphtalene-1-yloxy)-nicotinamide (intermediate 20, 148 mg, 0.500 mmol), 3,3-dimethylbutyraldehyde (75 mg, 0.750 mmol), and NaBH4 (38 mg, 1.00 mmol) gives the title compound (130 mg) as a white foam. Mass spectrum (ion spray): m/z=382 (M+1); 1HNMR (CDCl3): 8.55 (s, 1H), 8.14 (d, 1H), 7.22-7.14 (m, 2H), 6.90 (m, 2H), 5.76 (br. s, 2H), 3.03 (m, 1H), 2.92-2.80 (m, 2H), 2.71-2.55 (m, 3H), 2.49-2.41 (m, 1H), 1.85-1.65 (m, 4H), 1.42 (t, 2H), 0.90 (s, 9H).

Sources & evidence

ORD record: ord-639eb12e1e24449387e94e22f8ae7c1e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101638B2

Reaction notes

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