Diisopropylethylamine → HCID 44817105, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(2,4-dichloro-phenyl)-6-ethyl-2methyl-pyrazolo[5,1-b]oxazole-7-carboxylic acid (Intermediate IA) (37 mg, 0.11 mmol, 1 eq.) in DMF (0.8 ml) is successively added cyclopropylmethyl-propylamine (0.017 ml, 0.12 mmol, 1.1 eq.), DIPEA (0.038 ml, 0.22 mmol, 2 eq.) and HATU (46 mg, 0.12 mmol, 1.1 eq.) at RT. The reaction mixture is heated at 50° C. for 2 h then poured into EtOAc and washed with K2CO3 2M in water (2×). The organic layer is dried over Na2SO4, filtered and concentrated to dryness and the resulting crude residue is purified by column chromatography (SiO2; gradient elution iso-hexane/EtOAc 6:1 to 1:1) to yield the title compound as a yellow oil. MS: m/z 434.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.90 (1H, d), 7.73 (1H, d), 7.65 (1H, dd), 3.46 (2H, t), 3.30 (2H, s), 2.70 (2H, q), 2.34 (3H, s), 1.60 (2H, m), 1.11 (3H, t), 1.02 (1H, m), 0.63 (3H, m), 0.48 (2H, m), 0.20 (2H, m).

Provenance & Evidence