Diisopropylamine → 1,1-Dimethylethyl 3-[[(5-chloro-2-thienyl)sulfonyl]({[2-(trimethylsilyl)ethyl]oxy}methyl)amino]-4-(methyloxy)-1H-indazole-1-carboxylate

HRID 1874657노트

반응식

HRID 1874657 반응식
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[N:12]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH3:29][Si:30]([CH3:37])([CH3:36])[CH2:31][CH2:32][O:33][CH2:34]Cl.C(NC(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:34][O:33][CH2:32][CH2:31][Si:30]([CH3:37])([CH3:36])[CH3:29])[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[N:12]=2)(=[O:8])=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 594559961,1-Dimethylethyl 3-{[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazole-1-carboxylate

생성물 1

HCID 580544941,1-Dimethylethyl 3-[[(5-chloro-2-thienyl)sulfonyl]({[2-(trimethylsilyl)ethyl]oxy}methyl)amino]-4-(methyloxy)-1H-indazole-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,1-dimethylethyl 3-{[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazole-1-carboxylate (for a preparation see Intermediate 6) (2.21 g, 4.98 mmol) in DCM (20 mL) was added at 0° C. 2-(trimethylsilyl)ethoxymethyl chloride (1.23 mL, 6.97 mmol). Then was added at 0° C. in a dropwise fashion diisopropylamine (1.419 mL, 9.96 mmol) and the reaction mixture was stirred at room temperature. The reaction was quenched with water (50 mL), the organic layer was separated, and the aqueous layer was further extracted with 30 mL of DCM. The organic solutions were combined, dried with an hydrophobic frit and concentrated under reduced pressure to give a yellow oil that was used without further purification (3.12 g) LCMS (System A) RT=1.64 min, ES+ve m/z 574/576 (M+H)+.

후처리

  1. additionwas added at 0° C
  2. customThe reaction was quenched with water (50 mL)
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was further extracted with 30 mL of DCM
  5. customdried with an hydrophobic frit
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil that
  8. customwas used without further purification (3.12 g) LCMS (System A) RT=1.64 min, ES+ve m/z 574/576 (M+H)+

출처 및 근거

ORD 기록
ord-eeb4ae0344f84843b7e8ae6bbaaef812
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304446B2

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