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

HRID 38093노트

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HRID 38093 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][CH:15]=[CH:16][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCOCC1.O.O.[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[CH:16]=[CH:15][S:14][C:13]=23)=[CH:23][CH:22]=1

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 674230846-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole

생성물 1

HCID 674239983-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine수율 68.6%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
100 °C

실험 절차

6-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole (410 mg, 1.272 mmol) was dissolved in a 3:1 dioxane/water mixture (8 mL). Zinc powder (333 mg, 5.094 mmol, 4 eq) and ammonium chloride (680 mg, 12.72 mmol, 10 eq) were added and the mixture was stirred at 100° C. for 2 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. The crude product was purified by chromatography on silica gel (DCM/MeOH 97:3) to give 255 mg (68%) of 3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine as white solid.

후처리

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washCombined organic layers were washed with sat. aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (DCM/MeOH 97:3)

출처 및 근거

ORD 기록
ord-d67425bcdd5e47818c01ea2b655a50cc
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

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