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Methanol → N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)methanesulfonamide

HRID 1477861
ノート
印刷プレビュー

反応式

HRID 1477861 の反応式
[Li+].[BH4-].CO.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([N:28](COCC[Si](C)(C)C)[S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[N:20]2)([CH2:17][CH3:18])[C:13](OC)=O)=[CH:8][CH:7]=1>C1COCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[N:20]2)([CH:13]2[CH2:8][CH:9]2[C:12]#[N:19])[CH2:17][CH3:18])=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 70565947methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate

生成物 1

HCID 57524237N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)methanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of LiBH4 (120 mg, 5.43 mmol) in THF (5 mL) was added MeOH (174 mg, 5.43 mmol) and a solution of methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate (600 mg, 1.09 mmol) in THF (8 mL) followed. The mixture was stirred at room temperature for 2 h. The solution was quenched with saturated NH4Cl solution, and extracted with ethyl acetate (30 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=3/1) to afford the title compound as a pale yellow solid. LC/MS m/z=524.2 [M+H]+.

後処理

  1. customThe solution was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=3/1)

出典と根拠

ORDレコード
ord-880d68830cc04dd8b8f0c3cd973bfa47
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403807B2

反応ノート

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