Ammonium Chloride → 6-(3-Amino-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid ethyl ester

HRID 38095

反応式

[CH2:1]([O:3][C:4]([C:6]1[N:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[C:11]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:8]2[S:9][CH:10]=1)=[O:5])[CH3:2].[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCOCC1.O.O.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[N:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=3)[C:11]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[C:8]2[S:9][CH:10]=1)=[O:5])[CH3:2]

参加物

反応条件

温度: 100 °C

実験手順

6-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid ethyl ester (200 mg, 0.508 mmol) was dissolved in a 5:1 dioxane/water mixture (3 mL). Zinc powder (133 mg, 2.03 mmol, 4 eq) and ammonium chloride (271 mg, 5.08 mmol, 10 eq) were added and the mixture was stirred at 100° C. After 4 hours an addition of Zinc powder was made (37 mg) and heating was continued for 1.5 more hours. It was then diluted with water, made basic by addition of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×20 mL). Combined organic layers were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure. 82 mg of 6-(3-amino-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid ethyl ester were obtained as off-white solid, which was used without purification in the following step.

後処理

temperatureheating
extractionextracted with ethyl acetate (3×20 mL)
washCombined organic layers were washed with sat. aq. NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード: ord-5888b298a98f40cc849fe7fe446253fb
出典データセット: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08524707B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

関連ノート