Acetic Acid → (S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-methyl-2-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

HRID 867552Notes

Reaction equation

HRID 867552 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][N:9]3[CH2:24][CH2:23][CH2:22][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH:18][CH2:19][C:20]#[CH:21])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)(=[O:27])C>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.O>[Cl:1][C:2]1[C:7]2[C:8](=[O:27])[N:9]3[CH2:24][CH2:23][CH2:22][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:20]([CH3:21])=[CH:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 54413206(S)-8-chloro-11,12,13,13a-tetrahydro-N-(2-propynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 53703923(S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-methyl-2-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 962WaterSolvent

Procedure

3.5 g (10 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-N-(2-propynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide, 30 mg of mercury (II) acetate and 20 ml of glacial acetic acid are heated to reflux for 5 hours. The solution obtained is then poured into water and extracted three times with methylene chloride. The combined organic phases are dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with methylene chloride and 10% methanol and there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-methyl-2-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 228°-230°.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe solution obtained
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. washwhile eluting with methylene chloride and 10% methanol

Sources & evidence

ORD record
ord-5109044965fd46ed9efe7d0abb838473
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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