Acetic Anhydride → HCID 21265973, compound

HRID 566311Notes

Reaction equation

HRID 566311 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]3[CH:19]=C(CO)[N:21]=[C:17]3[CH2:16][N:15]=[C:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:13]=2[CH:31]=1>N1C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[N:21]=[C:17]2[CH2:16][N:15]=[C:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:13]3[CH:31]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=3[N:18]2[CH:19]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4192174HCID 4192174, compound

Product 1

HCID 21265973HCID 21265973, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.96 ml of acetic anhydride was added dropwise to a solution of 1.36 g of 8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-2-methanol in 30 ml of pyridine. The reaction mixture was stirred at room temperature for 70 h. and then evaporated in a vacuum. The residue was treated with saturated aqueous sodium hydrogen carbonate solution and this was extracted twice with dichloromethane. The dichloromethane extracts were dried over sodium sulphate and the solution was chromatographed over 50 g of silica gel. 1.4 g of an oil were eluted with dichloromethane/ethanol 197:3 and this was crystallized from diethyl ether/diisopropyl ether. There were obtained 2.1 g of 2-acetoxymethyl-8-chloro-6-(2-fluorophenyl)-4H-imidazo [1,2-a][1,4]benzodiazepine of m.p. 134-136° C. which was converted into the hydrochloride.

Workup

  1. customevaporated in a vacuum
  2. additionThe residue was treated with saturated aqueous sodium hydrogen carbonate solution
  3. extractionthis was extracted twice with dichloromethane
  4. dry with materialThe dichloromethane extracts were dried over sodium sulphate
  5. customthe solution was chromatographed over 50 g of silica gel
  6. wash1.4 g of an oil were eluted with dichloromethane/ethanol 197:3
  7. customthis was crystallized from diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-f12ea9f067a34d5a85408816d71facba
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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