Morpholine → HCID 14699765、化合物

HRID 2108061ノート

反応式

HRID 2108061 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=O)[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH3:27])[N:9]=1.ON1C2C=CC=CC=2N=N1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[O:22])[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH3:27])[N:9]=1

参加物

6

反応物 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14699764HCID 14699764、化合物

生成物 1

HCID 14699765HCID 14699765、化合物収率 60.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1.4 g of 3-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid in 20 ml of dimethylformamide are added 0.5 g of N-hydroxybenzotriazole and 0.35 g of morpholine and stirred at room temperature for 10 minutes. To the mixture is added 0.9 g of dicyclohexyl carbodiimide under ice-cooling and stirred for 3 hours and furthermore stirred at room temperature for 18 hours. The resulting dicyclohexylurea is filtered off, the filtrate is concentrated under reduced pressure and then the residue is dissolved in 100 ml of chloroform. The solution is washed with 50 ml of 5% aqueous sodium hydrogencarbonate solution and water and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the residue is crystallized from isopropyl ether. The precipitated crystals are collected by filtration and recrystallized from ethyl acetate to give 1 g of 3-[4 -(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid morpholide as colorless crystals, melting at 162°-163° C.

後処理

  1. temperaturecooling
  2. stirringstirred for 3 hours
  3. stirringfurthermore stirred at room temperature for 18 hours
  4. filtrationThe resulting dicyclohexylurea is filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionthe residue is dissolved in 100 ml of chloroform
  7. washThe solution is washed with 50 ml of 5% aqueous sodium hydrogencarbonate solution and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter separating by filtration
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customthe residue is crystallized from isopropyl ether
  12. filtrationThe precipitated crystals are collected by filtration
  13. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-eb49e83d27f84b3389a601c2487a8ac4
出典データセット
uspto-grants-1990_06
特許番号
US04937240

反応ノート

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