5-(furan-2-yl)-4H-pyrazole-3-carboxylic acid → HCID 178509583, compound

HRID 872522Notes

Reaction equation

HRID 872522 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:7][C:8]([C:11]([OH:13])=O)=[N:9][N:10]=1.[NH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1>>[Cl:30][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][CH2:15][NH:14][C:11]([C:8]3[NH:9][N:10]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[CH:7]=3)=[O:13])[N:18]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

3

Reactant 2

HCID 27716225-(furan-2-yl)-4H-pyrazole-3-carboxylic acidHCID 671701664-(1-(2-Aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 178509583HCID 178509583, compoundYield 36%

Procedure

The title compound was prepared using the method of Example 54 but starting from 5-(2-furyl)-4H-pyrazole-3-carboxylic acid (36 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 29 mg (36%) of the title compound. 1H-NMR (400 MHz; d1-CDCl3): δ 3.90-3.96 (m, 2H), 4.41 (t, 2H), 6.51-6.53 (m, 1H), 6.61 (d, 1H), 6.66 (d, 1H), 6.95 (s, 1H), 7.48-7.50 (m, 2H), 7.61 (broad s, 1H), 7.68 (d, 1H), 7.76-7.79 (m, 1H), 8.11 (s, 1H), 10.45 (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-5eaa8dc3f46e427983548cc6da26d60e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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