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

HRID 1874657ノート

反応式

HRID 1874657 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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)+

出典と根拠

ORDレコード
ord-eeb4ae0344f84843b7e8ae6bbaaef812
出典データセット
uspto-grants-2012_11
特許番号
US08304446B2

反応ノート

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