Isobutylamine → 2-(4-(5-(ethoxymethyl)pyridin-3-yl)phenyl)-N-isobutyl-2-methylpropanamide

HRID 1175592Notes

Reaction equation

HRID 1175592 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=O)=[CH:13][CH:12]=2)[CH:8]=[N:9][CH:10]=1)[CH3:2].[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH3:22])([CH3:21])[C:18]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])=[CH:15][CH:16]=2)[CH:8]=[N:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6558IsobutylamineHCID 687762972-(4-(5-(Ethoxymethyl)pyridin-3-yl)phenyl)-2-methylpropanoic acid

Product 1

HCID 160052282-(4-(5-(ethoxymethyl)pyridin-3-yl)phenyl)-N-isobutyl-2-methylpropanamideYield 80%

Procedure

Prepared in a similar manner to Example 3 from 2-(4-(5-(ethoxymethyl)pyridin-3-yl)phenyl)-2-methylpropanoic acid (example 26a) and isobutylamine. Yield: 80%. 1H NMR (400 MHz, dMSO): δ 0.72 (s, 3H); 0.74 (s, 3H); 1.15 (t, 3H, J=6.8); 1.46 (s, 6H); 1.68 (m, 1H); 2.83 (t, 2H, J=5.6); 3.51 (q, 2H, J=7.2); 4.54 (s, 2H); 7.4 (t, 1H); 7.41 (d, 2H, J=6.4); 7.66 (d, 2H, J=6.8); 7.95 (t, 1H, J=2.4); 8.49 (d, 1H, J=1.6); 8.78 (d, 1H, J=2.8). MS (M+H, 355).

Sources & evidence

ORD record
ord-e3d461091a13491baaf64c5a0ee0e67f
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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