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

反応式

[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]

参加物

反応物 3

HCID 176Acetic Acid

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

HCID 178434675HCID 178434675、化合物

生成物 1

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

実験手順

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).