Hydrochloric Acid → HCID 22439189, compound

HRID 963058Notes

Reaction equation

HRID 963058 reaction equation
[OH:1][CH2:2][C:3]1[N:7]2[C:8]3[S:22][C:21]([CH2:23][CH3:24])=[CH:20][C:9]=3[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N:11][CH2:12][C:6]2=[N:5][N:4]=1.Cl.C(=O)([O-])[OH:27].[Na+].[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[C:32]1[C:40](Cl)=[O:41]>C(Cl)(Cl)Cl>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]([C:9]1[CH:20]=[C:21]([CH2:23][CH3:24])[S:22][C:8]=1[N:7]1[C:6]([CH2:12][NH:11][C:40]([C:32]2[NH:31][C:39]3[C:34]([CH:33]=2)=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:41])=[N:5][N:4]=[C:3]1[CH2:2][OH:1])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118162081H-indole-2-carbonyl ChlorideHCID 67727793[4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-9-yl]methanol

Product 1

HCID 22439189HCID 22439189, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9-Hydroxymethyl-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (0.5 g) which can be synthesized by a known method (Japanese Patent Unexamined Publication No. 102698/1974) was stirred with 5% hydrochloric acid (10 ml) at 60° C. overnight. Then, sodium hydrogencarbonate was added to the reaction mixture to make the mixture alkaline. Chloroform and indole-2-carbonyl chloride (0.35 g) were added, and the mixture was stirred under ice-cooling for 3 hours. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin-layer chromatography (developing solvent:ethyl acetate) and recrystallized from ethyl acetate-hexane to give 0.015 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl[1,2,4]triazol-5-ylmethyl)indole-2-carboxamide.

Workup

  1. temperaturecooling for 3 hours
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin-layer chromatography (developing solvent:ethyl acetate)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e5f3e45d3e214613b480869e875dade8
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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