Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66744240, 화합물

HRID 2364106노트

반응식

HRID 2364106 반응식
[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]=[N: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([CH2:26][CH2:27][N:22]([C:17]4[N:16]=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:23][CH2:24]3)[NH:1][C:2]=2[CH:6]=1

참가 물질

7

반응물 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 14788561-Pyrimidin-2-yl-piperidin-4-oneHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

생성물 1

HCID 66744240HCID 66744240, 화합물수율 74%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide (111 mg, 0.50 mmol), 1-(2-pyrimidinyl)-piperidin-4-one (266 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 was triturated with MeOH/EtOAc and collected by filtration to afford the title compound (141 mg, 74%) as a pale yellow solid:

후처리

  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 was triturated with MeOH/EtOAc
  7. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-15ce9f811fc74347a50cec8c6b92d1a1
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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