1,2-Dimethylpropylamine, (R)- → (R)-N-sec-butyl-2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanamide

HRID 1175586Notes

Reaction equation

HRID 1175586 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][CH:22](C)[C@H:23]([NH2:25])[CH3:24]>>[C@H:23]([NH:25][C:16](=[O:18])[C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:5]2[CH:6]=[N:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:14][CH:13]=1)([CH3:20])[CH3:19])([CH2:22][CH3:21])[CH3:24]

Participants

3

Reactant 2

HCID 69997861,2-Dimethylpropylamine, (R)-HCID 687764552-(4-(5-Cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid

Product 1

HCID 16005195(R)-N-sec-butyl-2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanamideYield 48%

Procedure

Prepared in a similar manner to Example 3 from 2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid (example 21a) and (R)-3-Methyl-2-butylamine. Yield 48%. 1H NMR (400 MHz, DMSO): δ 0.71-0.73 (d, 3H), 0.74-0.76(d, 3H), 0.91-0.93 (d, 3H), 1.46 (s, 3H), 1.47 (s, 3H), 1.59 (m, 1H), 3.58 (m, 1H), 6.98-7.01 (d, 1H), 7.42-7.44 (d, 2H), 7.77-7.79 (d, 2H), 8.64 (s, 1H), 8.98 (s, 1H), 9.17 (s, 1H). MS (M+H, 336).

Sources & evidence

ORD record
ord-26886416e9a74b919702a3455062cc3d
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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