Dimethyl Sulfoxide → N-[(5-Bromopyridin-3-yl)methyl]-10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244205노트

반응식

HRID 2244205 반응식
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[Br:37][C:38]1[CH:39]=[C:40]([CH2:44][NH2:45])[CH:41]=[N:42][CH:43]=1.C(N(CC)CC)C.CS(C)=O>C(#N)C>[Br:37][C:38]1[CH:39]=[C:40]([CH2:44][NH:45][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH3:34])=[CH:25][CH:26]=4)=[O:20])[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13]3)=[CH:7][CH:6]=2)=[O:4])[CH:41]=[N:42][CH:43]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneHCID 229922643-(Aminomethyl)-5-bromopyridine

생성물 1

HCID 15953081N-[(5-Bromopyridin-3-yl)methyl]-10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide수율 44.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone (0.288 g, 0.534 mmol), (5-bromopyridin-3-yl)methylamine of Step C (0.20 g, 1.07 mmol), triethylamine (0.043 g, 0.588 mmol), dimethylsulfoxide (0.190 mL, 2.67 mmol), and acetonitrile (5 mL) was heated for 17 hours at an oil bath temperature of 81° C. The solvent was removed under reduced pressure and the resulting residue taken up in dichloromethane. The organics were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a yellow solid. The solid was triturated with hexane, diethyl ether, and ethyl acetate, collected by filtration, and dried under reduced pressure to give the title compound (0.145 g) as an off white solid, m.p 180-184° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. washThe organics were washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure to a yellow solid
  5. customThe solid was triturated with hexane, diethyl ether, and ethyl acetate
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-bae5c350b9c7477798dfe3902330a62c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678787B2

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