Triphenylphosphine Oxide → N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

HRID 1851564ノート

反応式

HRID 1851564 の反応式
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:36][N:37]([S:77]([C:80]1[S:81][CH:82]=[CH:83][CH:84]=1)(=[O:79])=[O:78])[C:38]1[CH:39]=[C:40]([O:72][C:73]([F:76])([F:75])[F:74])[CH:41]=[C:42]2[C:46]=1[NH:45][C:44]([C:47]([NH:49][CH2:50][CH2:51][S:52]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:43]2.C(=O)([O-])O.[Na+]>ClCCl>[S:52]1[CH2:51][CH2:50][N:49]=[C:47]1[C:44]1[NH:45][C:46]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:72][C:73]([F:76])([F:74])[F:75])=[CH:39][C:38]=2[N:37]([CH3:36])[S:77]([C:80]1[S:81][CH:82]=[CH:83][CH:84]=1)(=[O:79])=[O:78]

参加物

6

反応物 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 579017387-[Methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide

生成物 1

HCID 11978593N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide収率 82.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of triphenylphosphine oxide (0.37 g), trifluoromethanesulfonic anhydride (0.11 mL), and dichloromethane (5 mL) was stirred for 15 min under ice-cooling. Then, 7-[methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide (0.16 g) was added, and the mixture was stirred for 3 hr under ice-cooling. The reaction solution was poured into aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4-1:2), and the obtained crystals were washed with diethyl ether-hexane to give the title compound (84 mg, yield 82%) as colorless crystals. melting point 179-180° C.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hr under ice-
  3. temperaturecooling
  4. extractionextracted with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washthe obtained crystals were washed with diethyl ether-hexane

出典と根拠

ORDレコード
ord-61d1b90d22f24ba29e8e34d08c1373b7
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

読み込み中…