Dimethylformamide → (S)-1-(5-dibenzylaminomethyl-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 1377996Notes

Reaction equation

HRID 1377996 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=[C:33]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[CH3:46]N(C)C=O>>[CH2:38]([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)[CH2:46][C:33]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl 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 53962588(S)-1-(5-dibenzylaminomethyl-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 58%

Procedure

2.47 g (6.7 mmol) of crude (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, 9 ml (60 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) and 10.26 g (54 mmol) of benzyl bromide were stirred at room temperature overnight and at 50° for 6 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel while eluting with methylene chloride/methanol 19/1. After recrystallization from ethyl acetate and hexane there were obtained 2.16 g (58%) of (S)-1-(5-dibenzylaminomethyl-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 of m.p. 107°-109°.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel
  3. washwhile eluting with methylene chloride/methanol 19/1
  4. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-794279e07bcc49de8963d622df146a83
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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