5-(Pyridin-2-YL)-4H-pyrazole-3-carboxylic acid → N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)ethyl)-3-(pyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 872523Notes

Reaction equation

HRID 872523 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:8][C:9]([C:12]([OH:14])=O)=[N:10][N:11]=1.[NH2:15][CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[CH:24]=2)=[N:19]1>>[Cl:31][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][CH2:16][NH:15][C:12]([C:9]3[NH:10][N:11]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:8]=3)=[O:14])[N:19]=2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

3

Reactant 2

HCID 27716335-(Pyridin-2-YL)-4H-pyrazole-3-carboxylic acidHCID 671701664-(1-(2-Aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70655944N-(2-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)ethyl)-3-(pyridin-2-yl)-1H-pyrazole-5-carboxamideYield 23%

Procedure

The title compound was prepared using the method of Example 53 but starting from 5-pyridin-2-yl-4H-pyrazole-3-carboxylic acid (38 mg; 0.20 mmol) and 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (50 mg; 0.20 mmol). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% MeOH/DCM) to obtain 19 mg (23%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.70-3.74 (m, 2H), 4.38 (t, 2H), 6.96 (d, 1H), 7.23-7.40 (m, 2H), 7.82-8.02 (m, 5H), 8.09 (s, 1H), 8.48, (broad s, 1H), 8.62 (d, 1H), 13.89 (broad s, 1H).

Workup

  1. customThe title compound was prepared
  2. customCrude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% MeOH/DCM)

Sources & evidence

ORD record
ord-ff532eff454d4a84b9ac547b3e580d34
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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