3-acetyl-1H-pyrazole-5-carboxylic acid → HCID 67171427, compound

HRID 872524Notes

Reaction equation

HRID 872524 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)(=[O:3])[CH3:2].Cl.[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[O:25][C:24]([CH2:26][CH2:27][NH2:28])=[CH:23][CH:22]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]>>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:28][CH2:27][CH2:26][C:24]2[O:25][C:21]([C:16]3[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=3)=[CH:22][CH:23]=2)=[O:11])[NH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidHCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

Product 1

HCID 67171427HCID 67171427, compoundYield 50%

Procedure

The title compound was prepared using the method of Example 20 but starting from 3-acetyl-1H-pyrazole-5-carboxylic acid (215 mg; 1.37 mmol) and 2-(5-(3,4-dichlorophenyl)furan-2-yl)ethanamine hydrochloride (400 mg; 1.37 mmol). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane) to obtain 267 mg (50%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.50 (s, 3H—overlapping with DMSO), 2.93 (t, 2H), 3.54-3.60 (m, 2H), 6.33 (d, 1H), 7.02 (d, 1H), 7.30 (s, 1H), 7.58-7.64 (m, 2H), 7.82 (d, 1H), 8.65 (broad s, 1H), 14.21 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-1ebf2e438fc7425fae2ecddfe966133e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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