Allyl bromide → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one

HRID 1377997Notes

Reaction equation

HRID 1377997 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1.N12CCCN=C1CC[CH2:30][CH2:29][CH2:28]2.[CH2:38](Br)[CH:39]=[CH2:40]>CN(C)C=O>[CH2:30]([N:1]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1)[CH2:40][CH:39]=[CH2:38])[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54321795(S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Product 1

HCID 22876602(S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-oneYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g (8.1 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, 20 ml of N,N-dimethylformamide, 3 ml (20 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.5-5) and 6.54 g (54 mmol) of allyl bromide were stirred at 40° overnight. The reaction mixture was concentrated, the residue was dissolved in methylene chloride and the solution was washed with water. After drying the product was purified by chromatography on silica gel while eluting with melthylene chloride/methanol 19/1. There were obtained 1.8 g (49%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one, which was converted into the hydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed with water
  4. customAfter drying the product
  5. customwas purified by chromatography on silica gel
  6. washwhile eluting with melthylene chloride/methanol 19/1

Sources & evidence

ORD record
ord-1c7ef71e1d2942b289c083bc8ad2cc4d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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