Cyanomethylenetributylphosphorane → HCID 178503317、化合物

HRID 1269928

反応式

HRID 1269928 の反応式
[CH3:1][S:2][C:3]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2.O[C@H:14]1[CH2:19][CH2:18][C@H:17]([N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])[CH2:16][CH2:15]1.CS(C1C(OC2CCCN(C(OC(C)(C)C)=O)CC2)=CC=C2C=1C=NN2)(=O)=O.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[C:11]([O:12][C@@H:14]2[CH2:15][CH2:16][C@H:17]([N:20]3[C:21](=[O:30])[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:28]3=[O:29])[CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2

参加物

6

反応物 4

HCID 4622928CyanomethylenetributylphosphoraneHCID 229336484-(methylthio)-1H-indazol-5-olHCID 22933794HCID 22933794、化合物HCID 178515017HCID 178515017、化合物

生成物 1

HCID 178503317HCID 178503317、化合物収率 58%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

The 4-(methylthio)-1H-indazol-5-ol (0.166 g, 0.92 mmol) obtained in Example 607 and the trans-2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (0.151 g, 0.61 mmol) obtained in Example 323, (a) were added to a solution of cyanomethylenetri-n-butylphosphorane (0.247 g, 0.92 mmol) in toluene (6 ml), and the resulting mixture was heated at 100° C. and stirred for 7 hours. The reaction solution was concentrated and then diluted with chloroform, and a 1N-aqueous sodium hydroxide solution was added thereto, followed by extraction with chloroform (three times). The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel chromatography (hexane/ethyl acetate=2/1˜1/1) to obtain 2-(cis-4-{[4-(methylthio)-1H-indazol-5-yl]oxy}cyclohexyl)-1H-isoindole-1,3(2H)-dione (0.144 g: 58%).

後処理

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with chloroform
  3. additiona 1N-aqueous sodium hydroxide solution was added
  4. extractionfollowed by extraction with chloroform (three times)
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by a silica gel chromatography (hexane/ethyl acetate=2/1˜1/1)

出典と根拠

ORDレコード
ord-45618f7a7ec74444834daa30315ddd74
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

関連ノート

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