Sodium Hydroxide → HCID 67727725, compound

HRID 963050Notes

Reaction equation

HRID 963050 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][NH:24][C:25]([C:27]3[N:28]([CH2:36][C:37]([O:39]CC)=[O:38])[C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[OH-].[Na+]>CO>[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][NH:24][C:25]([C:27]3[N:28]([CH2:36][C:37]([OH:39])=[O:38])[C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67727699HCID 67727699, compound

Product 1

HCID 67727725HCID 67727725, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-ylmethylcarbamoyl)indole-1-acetate (0.83 g) obtained in Example 61 was dissolved in methanol (20 ml). A 2M aqueous sodium hydroxide solution (1.5 ml) was added, and the mixture was allowed to stand at room temperature for 4 hours. The reaction mixture was concentrated, and the residue was extracted with water. The aqueous layer was washed with ethyl acetate. Citric acid was added to adjust the aqueous layer to about pH 3.0, and the layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was crystallized from isopropyl ether to give 0.71 g of crude crystals. The crystals were recrystallized from ethyl acetate to give 0.63 g of 2-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-ylmethylcarbamoyl)indole-1-acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with water
  3. washThe aqueous layer was washed with ethyl acetate
  4. additionCitric acid was added
  5. extractionthe layer was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was crystallized from isopropyl ether
  10. customto give 0.71 g of crude crystals
  11. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7ccf43fe82b5477aa365a7dc4acba6e8
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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