5-(furan-2-yl)-4H-pyrazole-3-carboxylic acid → HCID 178422828, compound

HRID 872521Notes

Reaction equation

HRID 872521 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][C:15]([CH3:32])([CH3:31])[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]([CH3:30])[CH:23]=2)=[N:18]1>>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][C: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])([CH3:31])[CH3:32])[N:18]=2)=[CH:23][C:24]=1[CH3:30])#[N:27]

Participants

3

Reactant 2

HCID 27716225-(furan-2-yl)-4H-pyrazole-3-carboxylic acidHCID 671733754-(1-(2-amino-2-methylpropyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

Product 1

HCID 178422828HCID 178422828, compound

Procedure

The title compound was prepared using the method of Example 54 but starting from 5-(2-furyl)-4H-pyrazole-3-carboxylic acid (56 mg; 0.32 mmol) and 4-(1-(2-amino-2-methylpropyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile (80 mg; 0.32 mmol). Crude product was purified by chromatography (CombiFlash, silica-C18 column, eluent: 0-100% ACN/water) to obtain 16 mg of the product which was further purified by preparative HPLC (Waters Deltaprep 4000, SymmPrep 56.2, 25-80% ACN/AcONH4) to obtain 5.3 mg of he title compound. 1H-NMR (400 MHz; d1-CDCl3): δ 1.52 (s, 6H), 2.54 (s, 3H), 4.50 (s, 2H), 6.52 (dd, 1H), 6.57 (d, 1H), 6.64 (d, 1H), 6.90 (s, 1H), 7.44 (d, 1H), 7.48 (d, 1H), 7.59 (d, 1H), 7.70 (dd, 1H), 7.75 (d, 1H), 10.31 (broad s, 1H).

Workup

  1. customCrude product was purified by chromatography (CombiFlash, silica-C18 column, eluent: 0-100% ACN/water)

Sources & evidence

ORD record
ord-dc37585ed54f41e2a62bfcc457dce5cd
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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