Hydrochloric Acid → HCID 67727688, compound

HRID 963043Notes

Reaction equation

HRID 963043 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]([CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.Cl.C(=O)([O-])[OH:32].[Na+].[NH:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]1[C:45](Cl)=[O:46]>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]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[N:21][N:22]=[C:11]1[CH2:10][NH:9][C:45]([C:37]1[NH:36][C:44]2[C:39]([CH:38]=1)=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:46])=[O:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118162081H-indole-2-carbonyl ChlorideHCID 67727694HCID 67727694, compound

Product 1

HCID 67727688HCID 67727688, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(2-Chlorophenyl)-9-(2-ethoxycarbonylethyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (5.78 g) was heated with 5% hydrochloric acid for 3 hours, and the mixture was cooled to room temperature. Sodium hydrogencarbonate (25.2 g) and chloroform were added. Indole-2-carbonyl chloride (2.67 g) was added with vigorous stirring, and the mixture was stirred for 4 hours. The organic layer was concentrated, and the residue was dissolved in methanol (39 ml). The solution was hydrolyzed with 2M sodium hydroxide (3.9 ml) and the reaction mixture was made acidic. The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from ethanol to give 0.26 g of 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-(indole-2-carbonylaminomethyl) [1,2,4]triazol-5-yl)propionic acid.

Workup

  1. concentrationThe organic layer was concentrated
  2. dissolutionthe residue was dissolved in methanol (39 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b3a7be489b814246abcb51bc9cc2fc21
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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