1-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole → 6-[(3-Cyanopropoxy)]-N-[4-(5-cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]nicotinamide
Reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=1)#[N:2].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:26]=[C:25]([C:27]#[N:28])[N:24]([C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=3)[N:23]=2)[CH:17]=1>>[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:35][C:32]2[CH:31]=[CH:30][C:29]([N:24]3[C:25]([C:27]#[N:28])=[CH:26][C:22]([C:18]4[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=4)=[N:23]3)=[CH:34][CH:33]=2)=[O:13])=[CH:9][N:8]=1)#[N:2]Participants
3
Procedure
6-(3-cyanopropyloxy)nicotinic acid (0.6 mmol) was coupled with 3-(3-pyridyl)-5-cyano-1-(4′-aminophenyl)-pyrazole (0.5 mmol) under standard EDC mediated conditions (Method A). Standard work-up gave the title compound (142 mg, 62%), m.p. 190-191° C. 1H NMR(CDCl3): δ 2.04-2.11 (m, 2H), 2.67-2.70 (7, J=7.1 Hz, 2H), 4.42-4.5 (t, J=6.2 Hz, 2H), 6.98-7.00 (d, J=8.7 Hz, 1H), 7.53-7.56 (m, 1H), 7.82-7.84 (d, J=8.9 Hz, 2H), 8.02-8.04 (d, J=8.9 Hz, 2H), 8.1 (s, 1H), 8.28-8.32 (m, 2H), 8.63-8.64 (m, 1H), 8.82-8.83 (m, 1H), 9.15-9.16 (m, 1H), 10.6 (s, 1H).
Sources & evidence
- ORD record
- ord-9367b35c435740ffa15725b5bc315a95
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506747B1
Reaction notes
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