Pyrazolo[1,5-a]pyrimidine-2-carboxylic acid → N-(2-(5-(3,4-dichlorophenyl)furan-2-yl)ethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide

HRID 872526Notes

Reaction equation

HRID 872526 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]2=[CH:3][C:2]=1[C:10]([OH:12])=O.Cl.[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2[O:26][C:25]([CH2:27][CH2:28][NH2:29])=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]>>[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2[O:26][C:25]([CH2:27][CH2:28][NH:29][C:10]([C:2]3[CH:3]=[C:4]4[N:9]=[CH:8][CH:7]=[CH:6][N:5]4[N:1]=3)=[O:12])=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

3

Reactant 2

HCID 670824Pyrazolo[1,5-a]pyrimidine-2-carboxylic acidHCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

Product 1

HCID 67172275N-(2-(5-(3,4-dichlorophenyl)furan-2-yl)ethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamideYield 53.3%

Procedure

The title compound was prepared using the method of Example 20 but starting from pyrazolo[1,5-a]pyrimidinecarboxylic acid (82 mg; 0.5 mmol) and 2-(5-(3,4-dichlorophenyl)furan-2-yl)ethanamine hydrochloride (146 mg; 0.5 mmol). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-20% DCM/MeOH) to obtain 107 mg of the title compound. The product was further purified by trituration in toluene to give 55 mg of pure product (27%). 1H-NMR (400 MHz; d1-CDCl3): δ 3.06 (t, 2H), 3.83 (m, 2H), 6.233 (d, 1H), 6.61 (d, 1H), 6.93 (dd, 1H), 7.35-7.41 (m, 2H), 7.44 (dd, 1H), 7.70 (d, 1H), 8.55 (dd, 1H), 8.57-8.60 (m, 1H).

Workup

  1. customThe title compound was prepared
  2. customCrude product was purified by chromatography (CombiFlash, silica column, eluent: 0-20% DCM/MeOH)

Sources & evidence

ORD record
ord-7d3ce1550c6643779d2a70b0a413ae90
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…