Sodium Hydroxide → 2-[7-(4-Chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0,2,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetic acid

HRID 727258Notes

Reaction equation

HRID 727258 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C:10](C(OCC)=O)([CH2:24][C:25]([OH:27])=[O:26])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[CH:10]([CH2:24][C:25]([OH:27])=[O:26])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 197049582-(4-(4-Chlorophenyl)-6-(ethoxycarbonyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetic acid

Product 1

HCID 197049212-[7-(4-Chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0,2,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetic acidYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethanol (500 ml) is added to (±)-4-(4-chlorophenyl)-6-ethoxycarbonyl-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo-[4,3-a][1,4]diazepine-6-acetic acid (43 g), and the mixture is stirred at room temperature. 2N Sodium hydroxide (182 ml) is added and the mixture is stirred at 50° C. overnight. After the completion of the reaction, ethanol is distilled away, and the residue is adjusted to pH 4-5 with acetic acid. Then, the resulting mixture is stirred at 60° C. for 30 minutes and cooled to room temperature. The mixture is extracted with chloroform, and the organic layer is washed with saturated brine. The layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals are recrystallized from chloroform-methanol to give 20 g of (±)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo-[4,3-a][1,4]diazepine-6-acetic acid, melting point 287°-290° C.

Workup

  1. stirringthe mixture is stirred at 50° C. overnight
  2. distillationis distilled away
  3. stirringThen, the resulting mixture is stirred at 60° C. for 30 minutes
  4. temperaturecooled to room temperature
  5. extractionThe mixture is extracted with chloroform
  6. washthe organic layer is washed with saturated brine
  7. dry with materialThe layer is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crystals are recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-a935422147d046b585aecd40fb35ede7
Source dataset
uspto-grants-1998_01
Patent number
US05712274

Reaction notes

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