1-Bromopropane → HCID 70093436, compound

HRID 1378104Notes

Reaction equation

HRID 1378104 reaction equation
C(N(C(C)C)[CH:4]([CH3:6])[CH3:5])C.Br[CH2:11][CH2:12][CH3:13].[NH2:14][CH2:15][C:16]1[N:20]=[C:19]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[O:18][N:17]=1>CN(C)C=O>[CH2:11]([N:14]([CH2:15][C:16]1[N:20]=[C:19]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[O:18][N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 53986672HCID 53986672, compound

Product 1

HCID 70093436HCID 70093436, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 ml (8.6 mmol) of N-ethyldiisopropylamine and 1.1 ml (12 mmol) of 1-bromopropane were added to a solution of 600 mg (1.9 mmol) 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 in 20 ml of dimethylformamide and the mixture was stirred at 70° for 12 hours. The reaction solution was subsequently evaporated and 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 140:10:1). There were obtained 410 mg (54%) of (S)-1-(dipropylaminomethyl-1,2,4-oxadiazol-5-yl)-11,11 a-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=0.55 (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1).

Workup

  1. customThe reaction solution was subsequently evaporated
  2. customthe residue was 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 140:10:1)

Sources & evidence

ORD record
ord-643074e401554e2a9b81bae37afa8bb0
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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