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

HRID 61721ノート

反応式

HRID 61721 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-506c277519da482291685818c6d45abd
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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