Pentanal → HCID 59730143, compound

HRID 130972Notes

Reaction equation

HRID 130972 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5]([CH:20]([CH3:22])[CH3:21])=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=1.[CH:23](=O)[CH2:24][CH2:25][CH2:26][CH3:27].[BH4-].[Na+]>>[CH:20]([C:5]1[C:4]([CH2:3][CH2:2][NH:1][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 8063PentanalHCID 4311764Sodium borohydrideHCID 59730417HCID 59730417, compound

Product 1

HCID 59730143HCID 59730143, compoundYield 66.3%

Procedure

Using a method similar to Example 710, Step 4, using 6-[3-(2-amino-ethyl)-2-isopropyl-phenoxy]-nicotinamide (299 mg, 1.00 mmol), valeraldehyde (112 mg, 1.30 mmol), and NaBH4 (57 mg, 1.50 mmol) gave the title compound (245 mg) as a colorless glass. Mass spectrum (ion spray): m/z=370 (M+1); 1H NMR (DMSO-d6): 8.59 (s, 1H), 8.22 (d, 1H), 8.00 (s, 1H), 7.44 (s, 1H), 7.10 (t, 1H), 7.01 (m, 2H), 6.80 (d, 1H), 3.24 (m, 1H), 2.76 (m, 2H), 2.63 (m, 2H), 2.50 (m, 2H), 1.38 (m, 2H), 1.25 (m, 4H), 1.16 (d, 6H), 0.84 (t, 3H).

Sources & evidence

ORD record
ord-cc4086d66ab44fda8f8095afa1180ae0
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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