2-Furanmethanol, alpha-(aminomethyl)- → 2-(4-(5-cyanopyridin-3-yl)phenyl)-N-(2-(furan-2-yl)-2-hydroxyethyl)-2-methylpropanamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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:7][CH:8]=1)#[N:2].[NH2:21][CH2:22][CH:23]([C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)[OH:24]>>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([CH3:20])([CH3:19])[C:16]([NH:21][CH2:22][CH:23]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[OH:24])=[O:18])=[CH:13][CH:14]=2)[CH:6]=[N:7][CH:8]=1)#[N:2]Participants
3
Procedure
Prepared in a similar manner to Example 3 starting from 2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid (example 21a) and 2-amino-1-(furan-2-yl)ethanol. Yield: 75%. 1H NMR (400 MHz, DMSO): δ 1.41 (s, 6H), 3.26 (m, 1H), 3.41 (m, 1H), 4.63 (t, 1H), 5.45 (br-s, 1H), 6.21-6.22 (d, 1H), 6.35 (t, 1H), 7.34 (t, 3H), 7.35-7.37 (dd, 2H), 7.54-7.55 (d, 1H), 7.71-7.73 (dd, 2H), 8.61 (t, 1H), 8.97-8.98 (d, 1H), 9.15-9.16 (d, 1H). MS (M+H, 358).
Sources & evidence
- ORD record
- ord-a3ec99e90e3348c59338e99c6580ac1e
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842324B2
Reaction notes
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