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N,N'-Dimethylethylenediamine → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-2-cyano-1-(2-methanesulfonyl-pyridin-4-yl)-ethyl]-amide

HRID 1361206
ノート
印刷プレビュー

反応式

HRID 1361206 の反応式
Br[C:2]1[CH:7]=[C:6]([C@@H:8]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:9][C:10]#[N:11])[CH:5]=[CH:4][N:3]=1.[CH3:31][S:32]([O-:34])=[O:33].[Na+].CNCCNC.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.[I+].[Cu+]>[C:10]([CH2:9][C@H:8]([NH:12][C:13]([C:15]1[C:16]2[CH:23]=[N:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:17]=2[CH:18]=[N:19][CH:20]=1)=[O:14])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([S:32]([CH3:31])(=[O:34])=[O:33])[CH:7]=1)#[N:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 2733271Sodium methanesulfinateHCID 592782621-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-bromo-pyridin-4-yl)-2-cyano-ethyl]-amide

生成物 1

HCID 592782261-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-2-cyano-1-(2-methanesulfonyl-pyridin-4-yl)-ethyl]-amide

試薬・触媒・溶媒 3

HCID 178505377HCID 178505377、化合物触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
130 °C

実験手順

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-bromo-pyridin-4-yl)-2-cyano-ethyl]-amide (122 mg, 0.262 mmol), sodium methanesulfinate (53.5 mg, 0.524 mmol) and copper (I) iodine (99.8 mg, 0.524 mmol) in DMSO (2.5 mL) was evacuated and purged with argon three times and warmed at 130° C. After 45 minutes, the reaction was cooled to room temperature and N,N′-dimethylethylenediamine (112 μL, 1.05 mmol) was added. The mixture stirred for 30 minutes and was then diluted with ethyl acetate (20 mL), stirred for 15 minutes, and saturated aqueous ammonium chloride (20 mL) was added. The mixture was sonicated for 30 minutes, and was then diluted with ethyl acetate (100 mL). The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-8% methanol in CH2Cl2. The solid was further purified by HPLC using a C18 column and a gradient of 5-95% acetonitrile+0.1% TFA and water+0.1% TFA to afford the title compound. MS m/z 465.68 (MH+).

後処理

  1. custompurged with argon three times
  2. temperaturethe reaction was cooled to room temperature
  3. stirringstirred for 15 minutes
  4. customThe mixture was sonicated for 30 minutes
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (2×20 mL)
  7. washThe combined organic layers were washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was purified by silica gel chromatography
  12. washeluting with a gradient of 0-8% methanol in CH2Cl2
  13. customThe solid was further purified by HPLC

出典と根拠

ORDレコード
ord-0a49e07f11e140d991303927c3b51325
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879873B2

反応ノート

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