Hydrochloric Acid → Ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate

HRID 963101Notes

Reaction equation

HRID 963101 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][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:9]=1.Cl.C(=O)([O-])[OH:33].[Na+].[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[Cl:47])[C:41](Cl)=[O:42]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=1[N:12]1[C:20]([CH3:23])=[N:21][N:22]=[C:11]1[CH:10]([NH:9][C:41](=[O:42])[C:40]1[CH:44]=[CH:45][C:46]([Cl:47])=[C:38]([Cl:37])[CH:39]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 67727690ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate

Product 1

HCID 19085272Ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate (4.0 g) was added to 2M hydrochloric acid (100 ml), and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to 0° C. A saturated aqueous sodium hydrogencarbonate solution, chloroform and 3,4-dichlorobenzoyl chloride (2.1 g) were added, and the mixture was stirred for 0.5 hour. The organic layer was taken out, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) and crystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give 0.56 g of ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C
  2. stirringthe mixture was stirred for 0.5 hour
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)
  6. customcrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-802edad45e4246bda2847c0938b1b65b
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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