Acetic Acid → 3-(2,3-Dichlorobenzyl)-2-methyl-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-ol acetate

반응식

[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[C:6]([CH3:11])=[N:7][NH:8][C:9]=1[NH2:10].O=[C:18]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=O.C(O)(=[O:33])C>>[C:23]([O:22][C:20]1[N:8]2[N:7]=[C:6]([CH3:11])[C:5]([CH2:4][C:3]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:2]=3[Cl:1])=[C:9]2[N:10]=[C:18]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:19]=1)(=[O:33])[CH3:24]

참가 물질

반응물 3

HCID 176Acetic Acid

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

HCID 178434675HCID 178434675, 화합물

생성물 1

HCID 712709503-(2,3-Dichlorobenzyl)-2-methyl-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-ol acetate수율 60%

실험 절차

A mixture of 4-(2,3-dichlorobenzyl)-3-methyl-1H-pyrazol-5-amine (1.21 g, 4.72 mmol), ethyl 3-oxo-3-(pyridin-4-yl)propanoate (1.004 g, 5.195 mmol) in acetic acid (50 mL) was stirred under reflux overnight. After cooled to room temperature, the mixture was concentrated. The residue was diluted with ethyl acetate (20 mL). The resulting precipitate was filtered, washed with ethyl acetate, dried in vacuo to give the titled product (1.266 g, 60%); LC/MS: MS (ES+) m/e 385 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.91 (s, 3H), 2.12 (s, 3H), 4.16 (s, 2H), 6.10 (s, 1H), 6.91 (dd, J=1.2, 7.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.51 (dd, J=1.2, 7.8 Hz, 1H), 7.77 (d, J=5.7 Hz, 2H), 8.77 (d, J=5.7 Hz, 2H), 11.94 (s, 1H), 12.18 (s, 1H).