Dimethylformamide → HCID 22914350, compound

HRID 1378111Notes

Reaction equation

HRID 1378111 reaction equation
C(N([CH:7]([CH3:9])[CH3:8])C(C)C)C.[CH2:10](Br)[CH2:11][CH2:12][CH3:13].[NH2:15][CH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[N:23]=[CH:24][N:25]3[C:31]4[CH:32]=[CH:33][S:34][C:30]=4[C:29](=[O:35])[N:28]([CH3:36])[CH2:27][C:26]=23)[N:18]=1.[CH3:37]N(C)C=O>>[CH2:10]([N:15]([CH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[N:23]=[CH:24][N:25]3[C:31]4[CH:32]=[CH:33][S:34][C:30]=4[C:29](=[O:35])[N:28]([CH3:36])[CH2:27][C:26]=23)[N:18]=1)[CH2:37][CH2:9][CH2:7][CH3:8])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 81531DiisopropylethylamineHCID 22914212HCID 22914212, compound

Product 1

HCID 22914350HCID 22914350, compoundYield 36%

Procedure

2.35 ml (13.6 mmol) of N-ethyldiisopropylamine and 1.1 ml (10.2 mmol) of butyl bromide were added to a solution of 0.54 g (1.7 mmol) of 3-(5-aminomethyl-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 20 ml of dimethylformamide and the mixture was stirred at 70° for 1 hour. The reaction solution was subsequently evaporated, whereupon the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed three times with methylene chloride. The organic phases were dried with magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1). There were obtained 265 mg (36%) of 3-(5-dibutylaminomethyl-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 as a colourless foam, Rf=0.73 (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1).

Workup

  1. customThe reaction solution was subsequently evaporated, whereupon the residue
  2. customwas partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed three times with methylene chloride
  4. dry with materialThe organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1)

Sources & evidence

ORD record
ord-b54ac8b836dd4acb967e2bb2ececc537
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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