Dimethylformamide → HCID 54525087, compound

HRID 1378123Notes

Reaction equation

HRID 1378123 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].Cl[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:21]4[CH:22]=[CH:23][S:24][C:20]=4[C:19](=[O:25])[N:18]([CH3:26])[CH2:17][C:16]=23)[N:8]=1.[CH3:27]N(C)C=O>>[CH2:1]([NH:4][CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:21]4[CH:22]=[CH:23][S:24][C:20]=4[C:19](=[O:25])[N:18]4[CH2:26][CH2:27][C@H:17]4[C:16]=23)[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7852PropylamineHCID 22914381HCID 22914381, compound

Product 1

HCID 54525087HCID 54525087, compoundYield 80%

Procedure

0.73 ml (9 mmol) of propylamine was added to a suspension of 1 g (3 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one in 30 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 12 hours. The solution was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous solution was extracted with methylene chloride and the organic phases were dried, filtered and evaporated. The residue was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1). There was obtained 0.86 g (80%) of (S)-1-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-11,11a-dihydro-8H, 10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.38 (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. customthe organic phases were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1)

Sources & evidence

ORD record
ord-2a22639db4d64d6b97729f22928e3fed
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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