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

HRID 867539Notes

Reaction equation

HRID 867539 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([CH2:31][N+:32]#[C-:33])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][CH:33]=[N:32][CH:31]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 22840050(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo [1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde

Product 1

HCID 54538443(S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.51 g (5 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde, 1.07 g (5.5 mmol) of toluene-4-sulphonylmethyl isocyanide, 1 g of powdered potassium carbonate and 20 ml of methanol is heated to boiling under reflux for 2 hours. The mixture is then evaporated to a volume of 5 ml and the material obtained is chromatographed on silica gel while eluting with ethyl acetate/methanol (9:1). After recrystallization from ethyl acetate there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 201°-202°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. customThe mixture is then evaporated to a volume of 5 ml
  4. customthe material obtained
  5. customis chromatographed on silica gel
  6. washwhile eluting with ethyl acetate/methanol (9:1)
  7. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d4df0755cc3841bba34740793bb0f88a
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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