Hydrochloric Acid → 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)propionic acid

HRID 963099Notes

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[C:10]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])(C(OCC)=O)[N:9]=1.[OH-].[Na+].Cl>C(O)C>[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]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 4-(2-chlorophenyl)-6-(2-ethoxycarbonylethyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine-6-carboxylate (23 g) was dissolved in ethanol (92 ml). A 4M sodium hydroxide aqueous solution (92 ml) was added and the mixture was stirred at 60° C. for 6 hours. 2M Hydrochloric acid was added to adjust the aqueous solution to pH 2. The solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and concentrated. The obtained crystals were taken out, and washed with diisopropyl ether to give 13.5 g of 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)propionic acid.

Workup

extractionThe solution was extracted with ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
concentrationconcentrated
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-8f2f1ec1db424bafb9f5b752efbf35f8
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760032

Reaction notes

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