Ammonium Chloride → (+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine

HRID 2409012노트

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HRID 2409012 반응식
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:22]O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH:20]([NH2:22])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 1364090991-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime

생성물 1

HCID 86689823(+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine수율 87.4%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 887Methanol용매

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온도
80 °C

실험 절차

A mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime (1.29 g, 3.92 mmol), zinc (2.55 g, 39.2 mmol), and NH4Cl (2.10 mg, 39.2 mmol) in MeOH (5 mL) and HOAc (3 mL) was stirred at 80° C. for 4 h. The mixture was cooled to RT and the solid filtered. The filtrate was concentrated under reduced pressure. To the residue was added ammonia solution (50 mL) and the reaction mixture was extracted with DCM (3×50 mL). The combined organic extracts were concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (15:1:0.2) to afford 1.08 g (87.4%) (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine as a yellow solid: MS (ESI) m/z: 316.2 [M+1]+.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationthe solid filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added ammonia solution (50 mL)
  5. extractionthe reaction mixture was extracted with DCM (3×50 mL)
  6. concentrationThe combined organic extracts were concentrated under reduced pressure
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with DCM/MeOH/TEA (15:1:0.2)

출처 및 근거

ORD 기록
ord-69fc62f6eb1344dabe255071613d6ecf
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815877B2

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