Benzene → HCID 178466938、化合物

HRID 619184

反応式

HRID 619184 の反応式
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[CH:17]1([N:22]2[C:26]([NH2:27])=[C:25]([C:28]([NH2:30])=[O:29])[C:24]([CH2:31][CH3:32])=[N:23]2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C1C=CC=CC=1.O>[Pd].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC>[CH:17]1([N:22]2[C:26]3=[N:27][C:6]([C:5]4[CH:8]=[CH:9][C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:11][C:4]=4[O:3][CH2:1][CH3:2])=[N:30][C:28](=[O:29])[C:25]3=[C:24]([CH2:31][CH3:32])[NH:23]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

参加物

8

反応物 4

HCID 241BenzeneHCID 962WaterHCID 9587084-(Diethylamino)-2-ethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

生成物 1

HCID 178466938HCID 178466938、化合物収率 15.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 8058Hexane溶媒

実験手順

A mixture of 2-ethoxy-4-(diethylamino)benzaldehyde (7.87 g, 35.56 mmol), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.95 g, 17.78 mmol), p-toluenesulfonic acid monohydrate (0.05 g), 10% palladium on carbon (0.11 g) and benzene (150 ml) was refluxed overnight with the azeotropic removal of water. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was combined with that from a similar experimental run, and dissolved in CH2Cl2, and loaded onto a silica gel column. Elution of the column with ether/hexane (60/40) afforded a green foam which was titurated with refluxing hexane, and cooled and the product, as pale yellow needles, was collected by filtration to afford 1.19 g (8%) of 1-cyclopentyl-3-ethyl-6-[2-ethoxy-4-(diethylamino)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 138-139° C.

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutiondissolved in CH2Cl2
  4. washElution of the column with ether/hexane (60/40)
  5. customafforded a green foam which
  6. temperaturecooled
  7. filtrationthe product, as pale yellow needles, was collected by filtration

出典と根拠

ORDレコード
ord-7d482d272b9042e3b034bf1175e482ee
出典データセット
uspto-grants-1999_09
特許番号
US05958929

関連ノート

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