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p-Toluenesulfonic acid → N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-oxo-2-(4-oxo-1-piperidyl)ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 529857
ノート
印刷プレビュー

反応式

HRID 529857 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH:39]([F:41])[F:40])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][C:26]([N:28]3[CH2:37][CH2:36][C:31]4(OCC[O:32]4)[CH2:30][CH2:29]3)=[O:27])[N:9]=2)[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH:39]([F:40])[F:41])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][C:26](=[O:27])[N:28]3[CH2:29][CH2:30][C:31](=[O:32])[CH2:36][CH2:37]3)[N:9]=2)[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 118523245N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-oxo-ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

生成物 1

HCID 118522668N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-oxo-2-(4-oxo-1-piperidyl)ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide収率 45.3%

試薬・触媒・溶媒 1

HCID 180Acetone
溶媒

実験手順

To a solution of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-oxo-ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (1.01 g, 1.72 mmol) in acetone (20 mL) was added p-toluenesulfonic acid (359 mg, 2.06 mmol) and refluxed for 6 hours. LC/MS (method 31) shows product and presence of minor amounts of starting material. The reaction was cooled to room temperature and quenched with water. This was then extracted with ethyl acetate, dried with solid anhydrous magnesium sulfate powder and filtered to give a red oil. This was then purified by ISCO with a silica column and eluted with 0-15% methanol in dichloromethane to afford 0.43 g (0.78 mmol) of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-oxo-2-(4-oxo-1-piperidyl)ethyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide as a foamy off white solid. LC/MS (method 39) [M+H]+=544.1, RT=1.91 min.

後処理

  1. temperaturerefluxed for 6 hours
  2. customquenched with water
  3. extractionThis was then extracted with ethyl acetate
  4. dry with materialdried with solid anhydrous magnesium sulfate powder
  5. filtrationfiltered
  6. customto give a red oil
  7. customThis was then purified by ISCO with a silica column
  8. washeluted with 0-15% methanol in dichloromethane

出典と根拠

ORDレコード
ord-6d4b12b52c04418d9343b681ee15573f
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346815B2

反応ノート

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