2-Methylbutylamine → 2-methyl-N-(2-methylbutyl)-2-(4-(pyrimidin-5-yl)phenyl)propanamide

HRID 1175590Notes

Reaction equation

HRID 1175590 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=O.[CH3:19][CH:20]([CH2:23][CH3:24])[CH2:21][NH2:22]>>[CH3:6][C:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:9][CH:8]=1)([CH3:1])[C:3]([NH:22][CH2:21][CH:20]([CH3:19])[CH2:23][CH3:24])=[O:5]

Participants

3

Reactant 2

HCID 72832-MethylbutylamineHCID 687772492-Methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid

Product 1

HCID 160052272-methyl-N-(2-methylbutyl)-2-(4-(pyrimidin-5-yl)phenyl)propanamideYield 58%

Procedure

Prepared in a similar manner to Example 20 from 2-methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid (example 25a) and 2-methylbutan-1-amine. Yield: 58%. 1H NMR (400 MHz, dMSO): δ 0.72-0.74 (d, 3H), 0.79-0.84 (m, 3H) 0.97-1.00 (m, 1H), 1.24-1.27 (m, 1H), 1.47 (m, 1H), 1.48 (s, 6H), 2.81-2.87 (m, 1H), 2.93-2.98 (m, 1H), 7.37-7.39 (t, 1H), 7.44-7.47 (d, 2H), 7.76-7.79 (d, 2H), 9.13 (s, 1H), 9.18 (s, 1H); MS+H (312.1).

Sources & evidence

ORD record
ord-4dbca66eeb464f35b1aa359a3d9717d3
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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