Ammonium Chloride → 4-Benzothiazol-2-YL-N3-(2-ethylaminoethyl)-1H-pyrazole-3,5-diamine

HRID 1959806노트

반응식

HRID 1959806 반응식
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][CH2:8][CH2:9][NH:10][C:11](=O)[CH3:12])[C:3]=1[C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:3]1[C:4]([NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH3:12])=[N:5][NH:6][C:2]=1[NH2:1]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 66768089N-[2-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide

생성물 1

HCID 667680044-Benzothiazol-2-YL-N3-(2-ethylaminoethyl)-1H-pyrazole-3,5-diamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-[2-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide (80 mg, 0.25 mmol) and lithium aluminum hydride (92 mg) were refluxed in anhydrous THF (10 mL) for 3 hrs. The resulting mixture was poured into a saturated ammonium chloride solution (50 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield 54 mg of crude product. The crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=5:1 with 0.5% NH3. The title compound was isolated in a yield of 36 mg (48%). MS (m/z, ES+): 303.1 (M+1, 100%).

후처리

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto yield 54 mg of crude product
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-d8f366d899604dcda184d275b0e2b7a0
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410272B2

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