p-Toluenesulfonic acid → HCID 178437839、化合物

HRID 619142

反応式

HRID 619142 の反応式
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22](C=O)=[CH:23][CH:24]=1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:27]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][CH3:17])=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 312444-MethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

生成物 1

HCID 178437839HCID 178437839、化合物収率 127.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9 mmol), anisaldehyde (2.45 g, 18 mmol), xylenes (50 ml) and p-toluenesulfonic acid (0.5 g) was refluxed for 32 hours. The reaction mixture was stripped to dryness, treated with ethanol (100 ml) and then again concentrated to dryness. The residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml), the layers were separated and the aqueous layer was extracted with chloroform (3×100 ml). The combined organic layers were concentrated to approximately 25 ml and then combined with silica gel (30 g). The preloaded silica was placed on a silica gel column and eluted with ether/hexanes (8/10) to ether (100%) to afford 1.25 g (41%) of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 135-136° C., after recrystallization from cyclohexane.

後処理

  1. temperaturewas refluxed for 32 hours
  2. concentrationagain concentrated to dryness
  3. additionThe residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml)
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (3×100 ml)
  6. concentrationThe combined organic layers were concentrated to approximately 25 ml
  7. washeluted with ether/hexanes (8/10) to ether (100%)

出典と根拠

ORDレコード
ord-f214382a58004ada8dbfce96ae040665
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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