Diisopropylethylamine → 5-{(1R)-2-[[6-({4-[3-(Cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl](phenylmethyl)amino]-1-hydroxyethyl}-8-[(Phenylmethyl)oxy]-2(1H)-quinolinone

HRID 2118356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118356
[CH2:1]([NH:8][CH2:9][C@@H:10]([C:12]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:30])[NH:17]2)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([S:58]([CH:61]2[CH2:65][CH2:64][CH2:63][CH2:62]2)(=[O:60])=[O:59])[CH:53]=1>CC#N.O>[CH:61]1([S:58]([C:54]2[CH:53]=[C:52]([CH2:51][CH2:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C@@H:10]([C:12]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:18]4[C:13]=3[CH:14]=[CH:15][C:16](=[O:30])[NH:17]4)[OH:11])[CH:57]=[CH:56][CH:55]=2)(=[O:60])=[O:59])[CH2:65][CH2:64][CH2:63][CH2:62]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 691197205-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-oneHCID 691198271-{4-[(6-Bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene

Produkt 1

HCID 692041025-{(1R)-2-[[6-({4-[3-(Cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl](phenylmethyl)amino]-1-hydroxyethyl}-8-[(Phenylmethyl)oxy]-2(1H)-quinolinoneAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one (40 mg) was dissolved in MeCN (2 ml). N,N,-diisopropylethylamine (0.03 ml) and 1-{4-[(6-bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene (Example 1v) (30 mg) were added and the reaction mixture was heated at 80° under nitrogen for 48 h. The mixture was then diluted with water and extracted with EtOAc. The organic phases were combined, dried (MgSO4), and evaporated in vacuo. The residue was purified on a silica SPE bond elut cartridge, eluting with EtOAc-cyclohexane mixtures, to give the title compound, (13 mg)

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 80° under nitrogen for 48 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica SPE bond elut cartridge
  6. washeluting with EtOAc-cyclohexane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-79e09a63e0304bd29e944f2ebdba3dd1
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442839B2

Notizen zur Reaktion

Wird geladen…