Methylamine → 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378047Notes

Reaction equation

HRID 1378047 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:34])[N:9]([CH3:33])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:20][N:19]=[C:18]([CH2:21][N:22]4C(=O)C5=CC=CC=C5C4=O)[N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.CN>C(O)C>[NH2:22][CH2:21][C:18]1[N:17]=[C:16]([C:15]2[N:14]=[CH:13][N:12]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=4[C:8](=[O:34])[N:9]([CH3:33])[CH2:10][C:11]=23)[O:20][N:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22914227HCID 22914227, compound

Product 1

HCID 229142613-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

35.1 g (74 mmol) of 7-chloro-5,6-dihydro-5-methyl-3-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-4H-imidazo[1,5-a]-[1,4]benzodiazepin-6-one were stirred with 190 ml of methylamine in ethanol) and 100 ml of ethanol at 80° for 3 hours. The solution was concentrated, the residue was taken up in methylene chloride and 100 ml of 4N hydrochloric acid and the solution was washed three times with methylene chloride. The aqueous phase was made alkaline with 105 ml of 4N sodium hydroxide solution and extracted six times with methylene chloride. After drying the combined organic solutions and evaporating the solvent there were obtained 18.14 g (71%) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was used without further purification as the starting material for the Example described hereinafter.

Workup

  1. concentrationThe solution was concentrated
  2. wash100 ml of 4N hydrochloric acid and the solution was washed three times with methylene chloride
  3. extractionextracted six times with methylene chloride
  4. customAfter drying the combined organic solutions
  5. customevaporating the solvent there

Sources & evidence

ORD record
ord-39cce4b912134223a80a16acd9cce2c1
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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