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1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(4-(Cyanomethyl)tetrahydro-2H-thiopyran-4-yl)-3-((4-fluorophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 521213
ノート
印刷プレビュー

反応式

HRID 521213 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][NH:11][N:10]=2)=[CH:4][CH:3]=1.O=[S:18]1(=O)[CH2:23][CH2:22][C:21](=[CH:24][C:25]#[N:26])[CH2:20][CH2:19]1.C1CCN2C(=NCCC2)CC1>CC#N>[C:25]([CH2:24][C:21]1([N:11]2[CH:12]=[C:13]([C:14]([NH2:16])=[O:15])[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:10]2)[CH2:22][CH2:23][S:18][CH2:19][CH2:20]1)#[N:26]
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

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 617011612-(1,1-dioxidodihydro-2H-thiopyran-4(3H)-ylidene)acetonitrileHCID 178513765HCID 178513765、化合物2 回

生成物 1

HCID 715359871-(4-(Cyanomethyl)tetrahydro-2H-thiopyran-4-yl)-3-((4-fluorophenyl)amino)-1H-pyrazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

3-[(4-Fluorophenyl)amino]-1H-pyrazole-4-carboxamide (Intermediate 31-7) (100 mg, 0.45 mmol) was added to a mixture of 2-(1,1-dioxidodihydro-2H-thiopyran-4(3H)-ylidene)acetonitrile (160 mg, 0.91 mmol) in MeCN (1.51 mL). DBU (0.068 mL, 0.45 mmol) was then added, the reaction vessel was capped and the reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was cooled to ambient temperature, and purified by reverse phase preparative HPLC (using a gradient elution of MeCN/water, with 0.1% v/v TFA modifier). Desired fractions were combined, basified with saturated aqueous NaHCO3, and extracted with EtOAc. The organic layer was dried over anhydrous NaSO4, filtered, and concentrated in vacuo to afford the title compound, Example #7.

後処理

  1. customthe reaction vessel was capped
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. custompurified by reverse phase preparative HPLC (
  4. washa gradient elution of MeCN/water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-94be6161e58f4709bfb7180c0d923dd9
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328099B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート