Citric Acid → HCID 19085229, compound

HRID 963109Notes

Reaction equation

HRID 963109 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]([CH:18](C)[C:19](OC)=O)[S:17][C:13]=2[N:12]2[C:24]([CH3:27])=[N:25][N:26]=[C:11]2[CH2:10][N:9]=1.[C:28](=[O:31])([O-])[OH:29].[Na+].[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[C:34]1[C:42](Cl)=[O:43].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:48]>Cl.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][CH2:19][C:28]([OH:29])=[O:31])[S:17][C:13]=1[N:12]1[C:24]([CH3:27])=[N:25][N:26]=[C:11]1[CH2:10][NH:9][C:42]([C:34]1[NH:33][C:41]2[C:36]([CH:35]=1)=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:43])=[O:48]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 516892Sodium BicarbonateHCID 118162081H-indole-2-carbonyl ChlorideHCID 86752712HCID 86752712, compound

Product 1

HCID 19085229HCID 19085229, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent

Procedure

Methyl (4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-2-yl)propionate (1.0 g) was stirred in 2M hydrochloric acid (12 ml) at 60° C. for 3.5 hours. Then, sodium hydrogencarbonate was added to the reaction mixture to make the mixture alkaline. Chloroform and indole-2-carbonyl chloride (0.55 g) were added, and the mixture was stirred at room temperature for 2 hours. An aqueous citric acid solution was added to adjust the solution to pH 3. The obtained crystals were collected by filtration, washed with water and ethyl acetate, and dried to give 3-(3-(2-chlorobenzoyl)-2-(3-(2-indolecarbonylaminomethyl)-5-methyl[1,2,4]triazol-4-yl)thiophen-5-yl)propionic acid.

Workup

  1. filtrationThe obtained crystals were collected by filtration
  2. washwashed with water and ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-f717859d2b3b4a8c8fb2c35002e68848
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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