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

HRID 38073

반응식

HRID 38073 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-466421725f78485f95cc449635479323
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

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