Water → 1-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 971136ノート

反応式

HRID 971136 の反応式
Cl[C:2]1[C:3](=[O:8])[NH:4][CH2:5][CH2:6][CH:7]=1.Cl/[C:10](=[N:15]\[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)/[S:11]([CH3:14])(=[O:13])=[O:12].CCN(CC)CC.O>C1(C)C=CC=CC=1.CCOC(C)=O.C(Cl)Cl>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([N:16]2[C:2]3[C:3](=[O:8])[NH:4][CH2:5][CH2:6][C:7]=3[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:15]2)=[CH:22][CH:21]=1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 222404953-Chloro-5,6-dihydropyridin-2(1H)-oneHCID 22318579(1Z)-N-(4-Methoxyphenyl)-1-(methylsulfonyl)methanehydrazonoyl chloride

生成物 1

HCID 695158511-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one収率 31.4%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
85 °C

実験手順

Part A. 3-Chloro-5,6-dihydro-2(1H)-pyridinone (10.0 g, 38.17 mmol) and (1Z)-1-[chloro(methylsulfonyl)methylene]-2-(4-methoxyphenyl)hydrazine (5.0 g, 38.17 mmol) were stirred in toluene (200 mL) at RT under N2. Et3N (30 mL, 215.24 mmol) in toluene (150 mL) was added dropwise to the solution. After addition, the mixture was heated at 85° C. overnight. After cooling, H2O was added. It was extracted with EtOAc (2×). The organic layers were washed with H2O (2×) and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=1:1, then EtOAc) to give 1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (3.85 g, yield: 31%). LC/MS (ESI+) 322.4 (M+H)+, tR=1.79 min (10–90% CH3CN/H2O in a 4-min run).

後処理

  1. additionAfter addition
  2. temperatureAfter cooling
  3. extractionIt was extracted with EtOAc (2×)
  4. washThe organic layers were washed with H2O (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

出典と根拠

ORDレコード
ord-043fe4a4b0b84d588466a5d7a1ce95a0
出典データセット
uspto-grants-2007_12
特許番号
US07312214B2

反応ノート

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