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 1377997ノート

反応式

HRID 1377997 の反応式
[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]

参加物

5

反応物 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

生成物 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-one収率 49.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c7ef71e1d2942b289c083bc8ad2cc4d
出典データセット
uspto-grants-1997_09
特許番号
US05665718

反応ノート

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