Methylamine → HCID 54132471, compound

HRID 1378002Notes

Reaction equation

HRID 1378002 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[C:8]2[C:9](=[O:36])[N:10]3[CH2:35][CH2:34][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]3[O:21][N:20]=[C:19]([CH2:22][N:23]4C(=O)C5=CC=CC=C5C4=O)[N:18]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.CN>C(O)C>[NH2:23][CH2:22][C:19]1[N:18]=[C:17]([C:16]2[N:15]=[CH:14][N:13]3[C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:38])([F:37])[F:1])[C:8]=4[C:9](=[O:36])[N:10]4[CH2:35][CH2:34][C@H:11]4[C:12]=23)[O:21][N:20]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 54171952HCID 54171952, compound

Product 1

HCID 54132471HCID 54132471, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.3 g (10.2 mmol) of (S)-8-trifluoromethyl-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 70 ml of ethanol were treated dropwise with 150 ml of methylamine (33% in ethanol) at 60° within 45 min. The solution was stirred at 70° for 2 hours and subsequently concentrated. The residue was taken up in methylene chloride and 30 ml of 4N hydrochloric acid and the solution was washed three times with methylene chloride. The aqueous phase was made alkaline with 30 ml of 4N sodium hydroxide solution and extracted five times with methylene chloride. After drying the combined organic solutions and evaporating the solvent there were obtained 3.98 g (100%) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was used without further purification as the starting material for the Example described hereinafter.

Workup

  1. concentrationsubsequently concentrated
  2. wash30 ml of 4N hydrochloric acid and the solution was washed three times with methylene chloride
  3. extractionextracted five times with methylene chloride
  4. customAfter drying the combined organic solutions
  5. customevaporating the solvent there

Sources & evidence

ORD record
ord-bcdb47f636834c8e8bcebec09b4fe628
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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