Dimethyl Sulfoxide → 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375877ノート

反応式

HRID 375877 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2].CS(C)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.O>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:31][CH2:30][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 76688CyclohexanemethylamineHCID 212177041-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

生成物 1

HCID 212177061-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline (0.9 g, 3.3 mmol), DMSO (9 ml) and cyclohexanemethyl amine (0.86 ml, 6.6 mmol) was heated at 120°-130° C. for 6 hours. The reaction mixture was poured into water, acidified with acetic acid and the solid which formed was collected by filtration, dissolved in 5% NaOH and extracted with CH2Cl2 (2×50 ml). The aqueous layer was acidified with acetic acid and the solid which formed was collected by filtration and washed with water. The solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2 to afford 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid.

後処理

  1. temperaturewas heated at 120°-130° C. for 6 hours
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in 5% NaOH
  5. extractionextracted with CH2Cl2 (2×50 ml)
  6. customthe solid which formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customThe solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2

出典と根拠

ORDレコード
ord-bfa05063c31b45bb80a1fa67617994d7
出典データセット
uspto-grants-1996_01
特許番号
US05488055

反応ノート

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