Stannous chloride dihydrate → N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1969800노트

반응식

HRID 1969800 반응식
[CH:1]1([NH:7][C:8]2[C:9]3[CH:19]=[CH:18][NH:17][C:10]=3[N:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>CCO>[CH:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 58557102N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine

생성물 1

HCID 58557425N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine수율 87%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
55 °C

실험 절차

To a solution of N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (0.15 g, 0.57 mmol) in EtOH (10 mL) was added tin (II) chloride dihydrate (0.65 g, 2.9 mmol). The reaction mixture was heated at about 55° C. for about 1 h. The solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL) were added. The solid that formed was collected by vacuum filtration, washed with EtOAc (25 mL), and discarded. The filtrate was washed with saturated aqueous NaHCO3 (3×20 mL), dried over anhydrous MgSO4, filtered, and concd to give N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.107 g, 87%) as a brown residue: LC/MS (Table 1, Method c) Rt=1.21 min; MS m/z 231 (M+H)+.

후처리

  1. customThe solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL)
  2. additionwere added
  3. customThe solid that formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with EtOAc (25 mL)
  6. washThe filtrate was washed with saturated aqueous NaHCO3 (3×20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-25a3e11bbedd4cc7ad0f18db647444a1
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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