Potassium Hydroxide → HCID 9868167, compound

HRID 1744205Notes

Reaction equation

HRID 1744205 reaction equation
[CH2:1]([C:8]1[N:12]2[C:13]3[S:27][C:26]4[CH2:28][N:29](C(O)=O)[CH2:30][CH2:31][C:25]=4[C:14]=3[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[N:16][CH2:17][C:11]2=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([C:8]1[N:12]2[C:13]3[S:27][C:26]4[CH2:28][NH:29][CH2:30][CH2:31][C:25]=4[C:14]=3[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[N:16][CH2:17][C:11]2=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22227749HCID 22227749, compound

Product 1

HCID 9868167HCID 9868167, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing ethyl ester of 1-benzyl-6-(2-chlorophenyl)-7,10-dihydro-4H-pyrido[4′,3′;4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-9(8H)-carboxylic acid (3.6 g, 0.0071 mol) and potassium hydroxide (4.4 g, 0.078 mol) is heated under reflux in ethanol for 6 hours then left under agitation at ambient temperature for 48 hours. The solid is filtered on frit, washed with a minimum quantity of ethanol. After adding water, extraction is carried out with dichloromethane followed by drying over magnesium sulphate. The solvent is evaporated off and the product is purified by crystallization from an ethyl acetate/isopropanol 50/50 mixture, followed by leaving in a refrigerator for 48 hours then filtering on frit while washing with a solvent mixture: ethyl acetate-isopropanol (50-50). Washing is finally carried out with isopentene followed by drying under vacuum. 2.46 g (77%) of the desired product is obtained in the form of a beige coloured solid. Melting point: 191–192° C.

Workup

  1. temperatureis heated
  2. filtrationThe solid is filtered on frit
  3. washwashed with a minimum quantity of ethanol
  4. additionAfter adding
  5. extractionwater, extraction
  6. dry with materialby drying over magnesium sulphate
  7. customThe solvent is evaporated off
  8. customthe product is purified by crystallization from an ethyl acetate/isopropanol 50/50 mixture
  9. customby leaving in a refrigerator for 48 hours
  10. filtrationthen filtering on frit
  11. washwhile washing with a solvent mixture
  12. washWashing
  13. customby drying under vacuum

Sources & evidence

ORD record
ord-4549037f4eb64d6992cc053123cc85c6
Source dataset
uspto-grants-2006_03
Patent number
US07015213B1

Reaction notes

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