Methylamine → HCID 54219737, compound

HRID 1378042Notes

Reaction equation

HRID 1378042 reaction equation
CN.[O:3]=[C:4]1[N:10]2[CH2:11][CH2:12][CH2:13][C@H:9]2[C:8]2=[C:14]([C:17]3[O:21][N:20]=[C:19]([CH2:22][N:23]4C(=O)C5C(=CC=CC=5)C4=O)[N:18]=3)[N:15]=[CH:16][N:7]2[C:6]2[CH:34]=[CH:35][S:36][C:5]1=2>C(O)C>[NH2:23][CH2:22][C:19]1[N:18]=[C:17]([C:14]2[N:15]=[CH:16][N:7]3[C:6]4[CH:34]=[CH:35][S:36][C:5]=4[C:4](=[O:3])[N:10]4[CH2:11][CH2:12][CH2:13][C@H:9]4[C:8]=23)[O:21][N:20]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70073832HCID 70073832, compound

Product 1

HCID 54219737HCID 54219737, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 ml of methylamine (33% in ethanol) were added dropwise at 70° to a solution of 7.28 g (15.4 mmol) of (S)-2-[5-(8-oxo-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-1-yl)-1,2,4-oxadiazol-3-yl-methyl]-1,3-dihydro-isoindole-1,3-dione in 100 ml of ethanol and the mixture was stirred at 70° for a further two hours. The reaction mixture was evaporated and the residue was chromatographed (silica gel, methylene chloride/methanol 20:1). There were obtained 4.36 g (83%) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one as colourless crystals of m.p. 156°-158°.

Workup

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

Sources & evidence

ORD record
ord-52cf3a2346514e80ba4400fa9e18cd38
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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