3-Fluoropyridine-4-carboxylic acid → 3-{[4-(Propan-2-yloxy)benzyl]amino}pyridine-4-carboxylic acid
Reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[CH3:2][CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C:19]2[CH:20]=[N:21][CH:22]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])=[CH:9][CH:10]=1)[CH3:3]Participants
3
Procedure
The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287. Found 287.
Sources & evidence
- ORD record
- ord-321ec8dc580e439091c2754b41ec8a2d
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952151B2
Reaction notes
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