Trifluoroacetic acid → N-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamide

HRID 2275097노트

반응식

HRID 2275097 반응식
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:32])([CH3:31])[C:16]=2[CH:33]=1.C(N(C(C)C)CC)(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl.O>[C:29]([C:22]1[CH:21]=[C:20]2[C:25]([C:26]3[C:27](=[O:28])[C:15]4[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][NH:8][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:33][C:16]=4[C:17]([CH3:31])([CH3:32])[C:18]=3[NH:19]2)=[CH:24][CH:23]=1)#[N:30]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 668337928-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 66833850N-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamide수율 29%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid salt of 8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A8-2, 19 mg, 0.044 mmol) was suspended in dichloromethane (0.5 mL), added with diisopropylethylamine (0.0157 mL, 2 eq.) and methanesulfonyl chloride (0.0034 mL, 1 eq.), and then stirred at room temperature for 2 hr. The reaction solution was added to water, and then extracted with dichloromethane. After washing with saturated brine, the organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were separated by silica gel preparative TLC (ethyl acetate 100%) to obtain the target compound (5.5 mg, 29%).

후처리

  1. extractionextracted with dichloromethane
  2. washAfter washing with saturated brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere separated by silica gel preparative TLC (ethyl acetate 100%)

출처 및 근거

ORD 기록
ord-c53f95b123eb41a28f76113c53f91492
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126931B2

반응 노트

불러오는 중…