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Chloroform → 3-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide

HRID 6928
ノート
印刷プレビュー

反応式

HRID 6928 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1O[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[N:8][N:7]=1.[NH2:23][C:24]1[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH2:29])=[O:28].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C(Cl)(Cl)Cl>CN1CCN(C)C1=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:23]([C:24]2[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27]([NH2:29])=[O:28])[C:9]([C:11]2[CH:16]=[N:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:8][N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6212ChloroformHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 164957733-Amino-2-methylbenzamideHCID 220192365-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine

生成物 1

HCID 220192513-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide収率 56.1%

試薬・触媒・溶媒

1
HCID 66611,3-Dimethyl-2-imidazolidinone溶媒

反応条件

温度
200 °C

実験手順

5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine (1.0 g) prepared in the Reference Example 7 was dissolved in 1,3-dimethyl-2-imidazolidinone (10 ml), followed by addition of 3-amino-2-methylbenzamide (1.53 g) prepared in the Reference Example 6 and D-10-camphorsulfonic acid (290 mg), and stirred at 200° C. for 16 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, which was then washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1), to afford the entitled compound (812 mg, 56%). The physico-chemical values are as follows.

後処理

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. washwas then washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-1220b742e04a4582a13bd0b0471941a4
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07084164B2

反応ノート

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