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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 6'-(5-methyl-1H-pyrazol-4-yl)-1-(pyridin-2-yl)-1'H-spiro[piperidine-4,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2364109
ノート
印刷プレビュー

反応式

HRID 2364109 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH3:12])[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[CH3:12][C:11]1[NH:10][N:9]=[CH:8][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:25]3([CH2:24][CH2:23][N:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=4)[CH2:27][CH2:26]3)[NH:1][C:2]=2[CH:6]=1
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

7

反応物 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 183483911-(Pyridin-2-yl)piperidin-4-oneHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

生成物 1

HCID 66743797
6'-(5-methyl-1H-pyrazol-4-yl)-1-(pyridin-2-yl)-1'H-spiro[piperidine-4,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one
収率 77.3%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide (111 mg, 0.50 mmol), 1-(2-pyridyl)-piperidin-4-one (264 mg, 1.50 mmol), CSA (11.6 mg, 0.05 mmol), MgSO4 (120 mg, 1.00 mmol) and DMA (4 mL) was stirred at 100° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH). The obtained yellow solid (190 mg) was triturated with MeOH/EtOAc and collected by filtration to afford the title compound (147 mg, 77%) as a pale yellow solid:

後処理

  1. extractionextracted with 3:1 EtOAc/THF
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH)
  6. customThe obtained yellow solid (190 mg) was triturated with MeOH/EtOAc
  7. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-168e5f7fd8594748a797890fa41159be
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691828B2

反応ノート

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