alpha-Methyl-2-furanmethanamine → 2-(4-(6-cyanopyrazin-2-yl)phenyl)-N-(1-(furan-2-yl)ethyl)-2-methylpropanamide
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[CH:26]([NH2:28])[CH3:27]>>[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:28][CH:26]([C:22]3[O:21][CH:25]=[CH:24][CH:23]=3)[CH3:27])=[O:18])=[CH:13][CH:14]=2)[CH:6]=[N:5][CH:4]=1)#[N:2]Participants
3
Procedure
Prepared in a similar manner to Example 20 from 2-(4-(6-Cyanopyrazin-2-yl)phenyl)-2-methylpropanoic acid (example 20a) and 1-(furan-2-yl)ethanamine. Yield 35%. 1H NMR (400 MHz, dMSO): δ 1.32-1.33 (d, 3H), 1.49-1.52 (d, 6H), 5.09 (m, 1H), 6.06 (d, 1H), 6.33-6.35 (dd, 1H), 7.49-7.51 (d, 2H), 7.54 (d, 1H), 8.12-8.14 (d, 2H), 9.16 (s, 1H), 9.56 (s, 1H); MS+H (361).
Sources & evidence
- ORD record
- ord-88576478de17492ba199eef8a93f8dbf
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842324B2
Reaction notes
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