Dimethyl Sulfide → N-(1-(3-(Methylthio)benzyl)piperidin-3-yl)-1H-indazol-5-amine

HRID 656533노트

반응식

HRID 656533 반응식
CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21](=O)[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=4)[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.CSC>C1COCC1>[CH3:29][S:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[NH:5][N:6]=[CH:7]3)[CH2:16]1

참가 물질

4

반응물 2

HCID 1068Dimethyl SulfideHCID 597997742,2-Dimethyl-1-(5-(1-(3-(methylthio)benzoyl)piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one

생성물 1

HCID 57446046N-(1-(3-(Methylthio)benzyl)piperidin-3-yl)-1H-indazol-5-amine수율 41.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
60 °C

실험 절차

Into a round bottom flask was added 2,2-dimethyl-1-(5-(1-(3-(methylthio)benzoyl)-piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one (240 mg, 0.655 mmol) and THF (3 mL). The solution was heated to 60° C. and borane-dimethyl sulfide complex in THF (3.0 mL of a 2.0M solution in THF, 6.0 mmol) was added, allowing dimethyl sulfide to distill off. After the starting material was consumed, the reaction was evaporated, 5N NaOH (10 mL) was added, and the mixture was extracted with EtOAc. The organic phases were dried, evaporated, and the residue was chromatographed on silica gel, eluting with 3/1—EtOAc/Heptane to afford the title compound (95 mg, 41%).

후처리

  1. distillationto distill off
  2. customAfter the starting material was consumed
  3. customthe reaction was evaporated
  4. addition5N NaOH (10 mL) was added
  5. extractionthe mixture was extracted with EtOAc
  6. customThe organic phases were dried
  7. customevaporated
  8. customthe residue was chromatographed on silica gel
  9. washeluting with 3/1—EtOAc/Heptane

출처 및 근거

ORD 기록
ord-9b01b5d6c7a1485dac2586c9878aef59
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071779B2

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