Water → HCID 86752713, compound

HRID 963110Notes

Reaction equation

HRID 963110 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][C@@H:24]([C:37]1[N:41]2[C:42]3[S:56][C:55]([CH2:57][CH3:58])=[CH:54][C:43]=3[C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[Cl:53])=[N:45][CH2:46][C:40]2=[N:39][N:38]=1)[CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].[Cl:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[N:66]=[C:67]=[O:68].C(N(CC)CC)C.O>CN(C=O)C>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:44]1[C:43]2[CH:54]=[C:55]([CH2:57][CH3:58])[S:56][C:42]=2[N:41]2[C:37]([C@H:24]([NH:23][C:67]([NH:66][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=3[Cl:59])=[O:68])[CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[N:38][N:39]=[C:40]2[CH2:46][N:45]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76833Chlorophenyl isocyanateHCID 86752714HCID 86752714, compound

Product 1

HCID 86752713HCID 86752713, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl (R)-4-amino-4-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)butanoate di-p-toluenesulfonate (3.0 g) and 2-chlorophenyl isocyanate (0.46 ml) were dissolved in DMF (30 ml). Triethylamine (1.46 ml) was added and the mixture was stirred and water was added to the reaction mixture. The mixture was washed with an aqueous citric acid solution, saturated brine, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using ethyl acetate as an eluent to give 2.02 g of benzyl (R)-4-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)-4-(3-(2-chlorophenyl)ureido)butanoate.

Workup

  1. washThe mixture was washed with an aqueous citric acid solution, saturated brine
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3205a634e9a5458183e9baeaf4209993
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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