Methanesulfonic Acid → HCID 22914254, compound

HRID 1378088Notes

Reaction equation

HRID 1378088 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH:18][NH2:19])=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:22].[Cl:23][CH2:24][C:25](OC(=O)CCl)=O.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>CN(C)C=O.CCOCC>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:25]([CH2:24][Cl:23])=[N:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:22]

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 10946Chloroacetic anhydrideHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 67713662HCID 67713662, compound

Product 1

HCID 22914254HCID 22914254, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.50 g (0.00154 mol) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a ][1,4]benzodiazepine-3-carboxylic acid hydrazide in 5 ml of N,N-dimethylformamide was treated with 0.33 g (0.00193 mol) of chloroacetic anhydride. The solution obtained was stirred at room temperature for 11/2 hr., whereby a suspension resulted. The suspension was cooled to 0°, treated with 40 ml of ether and suction filtered. The white crystals obtained (0.643 g, m.p. 264°-266° (dec.)) were treated with 4.5 ml of methanesulphonic acid and 0.5 g of phosphorus pentoxide, whereupon the mixture warmed up and the solution was stirred at room temperature for 1 hr. The yellow solution was poured into 75 ml of ice-water, whereupon the mixture was made basic with aqueous sodium hydroxide solution and extracted with methylene chloride. The crystalline product was chromatographed over silica gel with ethyl acetate as the eluent. There was obtained 0.193 g (33%) of 7-chloro-3-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. :234°-236°.

Workup

  1. customThe solution obtained
  2. custom, whereby a suspension resulted
  3. temperatureThe suspension was cooled to 0°
  4. filtrationfiltered
  5. customThe white crystals obtained (0.643 g, m.p. 264°-266° (dec.))
  6. temperaturewarmed up
  7. stirringthe solution was stirred at room temperature for 1 hr
  8. extractionextracted with methylene chloride
  9. customThe crystalline product was chromatographed over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-f540f81fd4194df1b4f5e7ea12312de1
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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