1,2-Dimethylpropylamine, (R)- → (R)-2-methyl-N-(3-methylbutan-2-yl)-2-(4-(pyrimidin-5-yl)phenyl)propanamide

HRID 1175632Notes

Reaction equation

HRID 1175632 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]([CH3:24])[C@H:21]([NH2:23])[CH3:22]>>[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:23][C@@H:21]([CH:20]([CH3:24])[CH3:19])[CH3:22])=[O:5]

Participants

3

Reactant 2

HCID 69997861,2-Dimethylpropylamine, (R)-HCID 687772492-Methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid

Product 1

HCID 58789326(R)-2-methyl-N-(3-methylbutan-2-yl)-2-(4-(pyrimidin-5-yl)phenyl)propanamideYield 60%

Procedure

Prepared in a similar manner to Example 20 from 2-methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid (example 25a) and (R)-3-methylbutan-2-amine. Yield 60%. 1H NMR (400 MHz, dMSO): δ 0.74-0.79 (m, 6H), 0.94-0.96 (d, 3H), 1.48-1.49 (d, 6H), 1.59-1.64 (m, 1H), 3.59-3.65 (m, 1H), 6.99-7.02 (d, 1H), 7.44-7.45 (d, 2H), 7.77-7.80 (d, 2H), 9.14 (s, 1H), 9.18 (s, 1H); MS+H (312.1).

Sources & evidence

ORD record
ord-c4371ab9efc344a0a9bc8cfc406da93f
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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