Methylamine → HCID 53887943, compound

HRID 1377998Notes

Reaction equation

HRID 1377998 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:35])[N:9]3[CH2:34][CH2:33][C@H:10]3[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:35])[N:9]4[CH2:34][CH2:33][C@H:10]4[C:11]=23)[O:20][N:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 54532403HCID 54532403, compound

Product 1

HCID 53887943HCID 53887943, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.01 g (12.3 mmol) of (S)-8-chloro-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 were placed in 60 ml of ethanol and treated dropwise with 120 ml of methylamine (33% in ethanol) at 60° within 30 min. The solution was stirred at 70° for 2 hours and subsequently concentrated. By chromatography of the residue on silica gel while eluting with ethyl acetate/methanol 8/2 there were obtained 4.0 g (91%) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 206°-208°.

Workup

  1. concentrationsubsequently concentrated
  2. washBy chromatography of the residue on silica gel while eluting with ethyl acetate/methanol 8/2 there

Sources & evidence

ORD record
ord-5183d6f38dbf4153a70b360e3ac7e864
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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