1-Bromopropane → HCID 54134500, compound

HRID 1378105Notes

Reaction equation

HRID 1378105 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[O:20][N:19]=[C:18]([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][CH2:37][C@H:26]4[C:25]=23)[N:17]=1>CN(C)C=O>[CH2:11]([N:14]([CH2:15][C:16]1[O:20][N:19]=[C:18]([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][CH2:37][C@H:26]4[C:25]=23)[N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 53881593HCID 53881593, compound

Product 1

HCID 54134500HCID 54134500, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.74 ml (10 mmol) of N-ethyldiisopropylamine and 0.55 ml (6 mmol) of 1-bromopropane were added to a solution of 340 mg (1 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one in 10 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 240:10:1). There were obtained 162 mg (38%) of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one, Rf=0.26 (silica gel, ethyl acetate/methanol 40:1).

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 240:10:1)

Sources & evidence

ORD record
ord-576b48c4aba940f0a26d0a962a1883fe
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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