Ammonium Chloride → 3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine

HRID 38073

反応式

HRID 38073 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:13]3[S:14][CH2:15][CH2:16][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O1CCOCC1.O.[Cl-].[NH4+]>O.C(OCC)(=O)C.[Zn]>[N:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:10]([C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)=[N:11][N:12]3[CH2:16][CH2:15][S:14][C:13]=23)=[CH:23][CH:22]=1

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 218864351,4-Dioxane--water (1/1)HCID 674230366-(3-Nitro-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

生成物 1

HCID 469291833-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine収率 73.4%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

6-(3-Nitro-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole (150 mg, 0.463 mmol) was suspended in a 5:1 dioxane/water mixture (3 mL). Zinc powder (121 mg, 1.852 mmol, 4 eq) was added, followed by ammonium chloride (247 mg, 4.63 mmol, 10 eq) and the mixture was heated to 100° C. and stirred at the same temperature for 2 hours. The reaction mixture was then allowed to cool to room temperature and diluted with water and ethyl acetate. The aqueous phase was basified by adding solid Na2HPO4 and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried and concentrated to dryness. 100 mg of 3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine were obtained as off-white solid (73%).

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-466421725f78485f95cc449635479323
出典データセット
uspto-grants-2013_09
特許番号
US08524707B2

関連ノート

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