4-(Cyanopropyloxy)benzoic acid → 4-(3-cyanopropoxy)-N-[4-(5-cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]benzamide

HRID 1634101Notes

Reaction equation

HRID 1634101 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][CH: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:8]=[CH:9][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:14][CH:15]=1)#[N:2]

Participants

3

Reactant 2

HCID 146503364-(Cyanopropyloxy)benzoic acidHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole

Product 1

HCID 98037034-(3-cyanopropoxy)-N-[4-(5-cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]benzamide

Procedure

The 4-(cyanopropyloxy)benzoic acid (0.75 mmol) was coupled with 3-(3-pyridyl)-5-cyano-1-(4′-aminophenyl)-pyrazole (0.5 mmol) under standard EDC mediated conditions (Method A). The crude product was recrystallized from hot benzene/methanol, m.p. 193-194° C. 1H NMR(CDCl3): δ 2.04-2.11 (m, 2H), 2.68-2.71 (7, J=7.1 Hz, 2H), 4.14-4.17 (t, J=6 Hz, 2H), 7.11-7.13 (d, J=8.6 Hz, 2H), 7.53-7.56 (m, 1H), 7.79-7.82(d, J=8.7 Hz, 2H), 8.00-8.05 (m, 4H), 8.1 (s, 1H), 8.30-8.32 (d, J=8 Hz, 1H), 8.63-8.64(d, J=4.6 Hz, 1H), 9.15 (s, 1H), 10.4 (s, 1H).

Workup

  1. customThe crude product was recrystallized from hot benzene/methanol, m.p. 193-194° C

Sources & evidence

ORD record
ord-bdfa8440a492474e9ec2851b3b41de09
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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