Ro 19-4603 → 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylic acid

HRID 867564Notes

Reaction equation

HRID 867564 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[S:10][CH:11]=[CH:12][C:6]=2[N:5]2[CH:13]=[N:14][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:4]2[CH2:3]1>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[S:10][CH:11]=[CH:12][C:6]=2[N:5]2[CH:13]=[N:14][C:15]([C:16]([OH:18])=[O:17])=[C:4]2[CH2:3]1

Participants

3

Reactant 1

HCID 127382Ro 19-4603

Product 1

HCID 212899275,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylic acidYield 112%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7.2 g of tert.butyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate are dissolved in 100 ml of trifluoroacetic acid while cooling with ice and left to stand at room temperature for 90 minutes. The solution is then evaporated in vacuo and the residue is crystallized from ethyl acetate and diethyl ether. There are obtained 6.65 g of crude 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylic acid.

Workup

  1. temperaturewhile cooling with ice
  2. waitleft
  3. customThe solution is then evaporated in vacuo
  4. customthe residue is crystallized from ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-9bd9c09aae1440e5a74707af0f6d5700
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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