Diisopropylethylamine → 3-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide

HRID 749257Notes

Reaction equation

HRID 749257 reaction equation
[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][CH2:47][O:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[C:54]([S:58]([NH2:61])(=[O:60])=[O:59])[CH:55]=[CH:56][CH:57]=1>C(#N)C.O>[CH2:1]([N: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])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[C:54]([S:58]([NH2:61])(=[O:60])=[O:59])[CH:55]=[CH:56][CH:57]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 115093953-{3-[(7-Bromoheptyl)oxy]propyl}benzenesulfonamideHCID 691197205-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 693162143-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamideYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one (48 mg) was dissolved in acetonitrile (2 ml). N,N-diisopropylethylamine (0.042 ml), and 3-{3-[(7-bromoheptyl)oxy]propyl}benzenesulfonamide (43 mg) were added to the solution, which was heated at reflux for 72 h under nitrogen. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried (MgSO4) and evaporated in vacuo. The residue was purified on a silica SPE cartridge eluting with ethyl acetate-cyclohexane mixtures to give the title compound (36 mg). LCMS RT=2.76 min

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 h under nitrogen
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified on a silica SPE cartridge
  7. washeluting with ethyl acetate-cyclohexane mixtures

Sources & evidence

ORD record
ord-2607abdb2a9e4138b98ce0e74683c724
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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