Methylamine → HCID 53986672, compound

HRID 1378246Notes

Reaction equation

HRID 1378246 reaction equation
CN.[O:3]=[C:4]1[N:10]2[CH2:11][CH2:12][C@H:9]2[C:8]2=[C:13]([C:16]3[O:20][N:19]=[C:18]([CH2:21][N:22]4C(=O)C5C(=CC=CC=5)C4=O)[N:17]=3)[N:14]=[CH:15][N:7]2[C:6]2[CH:33]=[CH:34][S:35][C:5]1=2>C(O)C>[NH2:22][CH2:21][C:18]1[N:17]=[C:16]([C:13]2[N:14]=[CH:15][N:7]3[C:6]4[CH:33]=[CH:34][S:35][C:5]=4[C:4](=[O:3])[N:10]4[CH2:11][CH2:12][C@H:9]4[C:8]=23)[O:20][N:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 53633470HCID 53633470, compound

Product 1

HCID 53986672HCID 53986672, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 ml of methylamine (33% in ethanol) were added dropwise at 70° to a solution of 2.4 g (5.23 mmol) of (S)-2-[5-(8-oxo-11,11 a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-1-yl)-1,2,4-oxadiazol-3-yl-methyl]-2,3-dihydro-1H-isoindole-1,3-dione in 40 ml ethanol and the mixture was stirred at 70° for a further 2 hours. The reaction mixture was evaporated and the residue was chromatographed (silica gel, methylene chloride/methanol 20:1). There were obtained 1.60 g (93%) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as colourless crystals of m.p. 227° (dec.).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed (silica gel, methylene chloride/methanol 20:1)

Sources & evidence

ORD record
ord-1556c55b712b4d4ba5fd909822a9d0c6
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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