Methanol → HCID 178511734, 화합물

HRID 707380노트

반응식

HRID 707380 반응식
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=[CH:13]2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.CO>C(Cl)Cl.CCOC(C)=O>[N:12]1([C@H:10]2[CH2:9][C@H:8]([NH2:7])[CH2:11]2)[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

참가 물질

6

반응물 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 178454099HCID 178454099, 화합물

생성물 1

HCID 178511734HCID 178511734, 화합물수율 39.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To the solution of tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (294 mg, 1.02 mmol) in DCM (2.0 ml) was added trifluoroacetic acid, 99% (760 μl, 10.2 mmol). The reaction mixture was stirred at room temperature under N2 for 1 h. The solvent was evaporated and the residue was triturated with DCM three times, redissolved in DCM, and then treated with solid NaHCO3. The solid was filtered off and the filtrate concentrated in vacuo. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, then 15% MeOH in EtOAc, to provide trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutanamine (75 mg, 0.401 mmol, 39.2% yield) as light-yellow oil. ESI (M+1) 188.0.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was triturated with DCM three times
  3. dissolutionredissolved in DCM
  4. additiontreated with solid NaHCO3
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  8. washeluting with a gradient of 0% to 100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-516deb8a39714743b52a3f018d74afbd
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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