Morpholine → HCID 15106965, compound

HRID 2108066Notes

Reaction equation

HRID 2108066 reaction equation
[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](O)=[O:21])[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH2:27][CH3:28])[N:9]=1.ON1C2C=CC=CC=2N=N1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]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:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[O:21])[S:17][C:13]=2[N:12]2[C:23]([CH3:26])=[N:24][N:25]=[C:11]2[CH:10]([CH2:27][CH3:28])[N:9]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 15106958HCID 15106958, compound

Product 1

HCID 15106965HCID 15106965, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g of 3-[4-(2-chlorophenyl)-6-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propionic acid in 15 ml of dimethylformamide are added 0.4 g of N-hydroxybenzotriazole and 0.23 ml of morpholine and stirred at room temperature for 10 minutes. To the mixture is added 0.6 g of dicyclohexyl carbodiimide under ice-cooling and stirred for 1 hour and furthermore stirred at room temperature for 18 hours. The resulting dicyclohexylurea is filtered off and to the filtrate is added 100 ml of chloroform. The solution is washed with 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 a mixture of isopropyl ether-ethyl acetate (1:1) to give 0.8 g of 3-[4-(2-chlorophenyl)-6 -ethyl-9-methyl-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 145°-147° C.

Workup

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

Sources & evidence

ORD record
ord-d74a799093fe428c97b636c60a6cf0d3
Source dataset
uspto-grants-1990_06
Patent number
US04937240

Reaction notes

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