(R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl]amino]ethyl]-phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide → (R)-6-[[3-[[4-[2-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]ethyl]phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944977Notes

Reaction equation

HRID 1944977 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:66])[CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]3[CH:35]=[C:36]([S:40]([C:43]4[CH:44]=[C:45]5[C:50](=[C:51]([CH3:53])[CH:52]=4)[N:49]=[CH:48][C:47]([C:54]([NH2:56])=[O:55])=[C:46]5[NH:57][C:58]4[CH:63]=[CH:62][CH:61]=[C:60]([O:64][CH3:65])[CH:59]=4)(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=3)=[O:33])=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CCO.C1COCC1.[Pd]>[OH:66][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([C:34]2[CH:35]=[C:36]([S:40]([C:43]3[CH:44]=[C:45]4[C:50](=[C:51]([CH3:53])[CH:52]=3)[N:49]=[CH:48][C:47]([C:54]([NH2:56])=[O:55])=[C:46]4[NH:57][C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([O:64][CH3:65])[CH:59]=3)(=[O:41])=[O:42])[CH:37]=[CH:38][CH:39]=2)=[O:33])=[CH:29][CH:30]=1

Participants

5

Reactant 1

HCID 86659111(R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl]amino]ethyl]-phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 54588271(R)-6-[[3-[[4-[2-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]ethyl]phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamideYield 60.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolvent

Procedure

Intermediate 144 (119 mg) was dissolved in a mixture of EtOH (2 mL) and THF (3.5 mL) and hydrogenated in the presence of 10% Pd/C at rt and ambient pressure. After completion, the reaction was filtered and the filtrate purified by reverse-phase preparatory-LC to give the title compound as a yellow solid (65 mg).

Workup

  1. filtrationAfter completion, the reaction was filtered
  2. customthe filtrate purified by reverse-phase preparatory-LC

Sources & evidence

ORD record
ord-b92e282ea4d74fd2864f39902a590885
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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