3-Pentanamine → 2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methyl-N-(pentan-3-yl)propanamide

HRID 1175583Notes

Reaction equation

HRID 1175583 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=O)=[CH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1)#[N:2].[CH3:21][CH2:22][CH:23]([NH2:26])[CH2:24][CH3:25]>>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([CH3:20])([CH3:19])[C:16]([NH:26][CH:23]([CH2:24][CH3:25])[CH2:22][CH3:21])=[O:18])=[CH:13][CH:14]=2)[CH:6]=[N:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 120193-PentanamineHCID 687764552-(4-(5-Cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid

Product 1

HCID 160051942-(4-(5-cyanopyridin-3-yl)phenyl)-2-methyl-N-(pentan-3-yl)propanamideYield 55%

Procedure

Prepared in a similar manner to Example 3 from 2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid (example 21a) and 3-pentanamine. Yield 55%. 1H NMR (400 MHz, DMSO): δ 0.69-0.73 (t, 6H), 1.27 (m, 2H), 1.36 (m, 2H), 1.47 (s, 6H), 3.56 (m, 1H), 6.90-6.93 (d, 1H), 7.43-7.45 (d, 2H), 7.77-7.79 (d, 2H), 8.63-8.64 (t, 1H), 8.96-8.98 (d, 1H), 9.17-9.18 (d, 1H). MS (M+H, 336).

Sources & evidence

ORD record
ord-e043f3ab7b6547e4b73ff62596ab9e4f
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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