Furfurylamine → 2-(4-(6-cyanopyrazin-2-yl)phenyl)-N-(furan-2-ylmethyl)-2-methylpropanamide

HRID 1175637Notes

Reaction equation

HRID 1175637 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([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:5][CH:4]=1)#[N:2].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][NH2:27]>>[C:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([CH3:20])([CH3:19])[C:16]([NH:27][CH2:26][C:22]3[O:21][CH:25]=[CH:24][CH:23]=3)=[O:18])=[CH:13][CH:14]=2)[CH:6]=[N:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 3438FurfurylamineHCID 687764432-(4-(6-Cyanopyrazin-2-yl)phenyl)-2-methylpropanoic acid

Product 1

HCID 687765562-(4-(6-cyanopyrazin-2-yl)phenyl)-N-(furan-2-ylmethyl)-2-methylpropanamideYield 30%

Procedure

Prepared in a similar manner to Example 20 from 2-(4-(6-Cyanopyrazin-2-yl)phenyl)-2-methylpropanoic acid (example 20a) and furan-2-ylmethanamine. Yield 30%. 1H NMR (400 MHz, dMSO): δ 1.51 (s, 6H), 4.23-4.25 (d, 2H), 6.06-6.07 (d, 1H), 6.34-6.35 (t, 1H), 7.48-7.50 (d, 2H), 7.53 (t, 1H), 7.97-8.00 (t, 1H), 9.16 (s, 1H), 9.56 (s, 1H); MS+H (347).

Sources & evidence

ORD record
ord-3df2fe70493843cc9d7710ccdd830033
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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