Hydrochloric Acid → HCID 19085168, compound

HRID 963097Notes

Reaction equation

HRID 963097 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][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:9]=1.Cl.C(=O)([O-])[OH:32].[Na+].[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:40](Cl)=[O:41]>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:40](=[O:41])[C:39]1[CH:43]=[CH:44][C:45]([Cl:46])=[C:37]([Cl:36])[CH:38]=1)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 67727712HCID 67727712, compound

Product 1

HCID 19085168HCID 19085168, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)acetate (1.0 g) synthesized by a known method such as WO94/06802 was added to 2M hydrochloric acid (24 ml), and the mixture was stirred at 60° C. for 0.5 hour. The reaction mixture was cooled to 0° C. A saturated aqueous sodium hydrogencarbonate solution, chloroform and 3,4-dichlorobenzoyl chloride (0.53 g) were added and the mixture was stirred for 1 hour. The organic layer was taken out and dried over magnesium sulfate. The residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane) and crystallized from diisopropyl ether to give 0.06 g of ethyl 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-3-(3,4-dichlorobenzoylamino)propionate.

Workup

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

Sources & evidence

ORD record
ord-03311c4098c8464eb5a5de470f2215f9
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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