(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one → 6-[[3-[[3-[2-[[(R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]propyl]-N-methylbenzamido]methyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944978Notes

Reaction equation

[Si](O[C@H](C1C=CC(O)=C2C=1C=CC(=O)N2)CNCCCCCCCCNC(C1C=C(S(C2C=C3C(=C(C)C=2)N=CC(C(N)=O)=C3NC2C=CC=C(OC)C=2)(=O)=O)C=CC=1)=O)(C(C)(C)C)(C)C.[NH2:67][CH2:68][C@@H:69]([C:71]1[CH:80]=[CH:79][C:78]([OH:81])=[C:77]2[C:72]=1[CH:73]=[CH:74][C:75](=[O:82])[NH:76]2)[OH:70].[CH3:83][O:84][C:85]1[CH:86]=[C:87]([NH:91][C:92]2[C:101]3[C:96](=[C:97]([CH3:126])[CH:98]=[C:99]([S:102]([C:105]4[CH:110]=[CH:109][CH:108]=[C:107]([CH2:111][N:112]([C:114]([C:116]5[CH:121]=[CH:120][CH:119]=[C:118]([CH2:122][C:123](=O)[CH3:124])[CH:117]=5)=[O:115])[CH3:113])[CH:106]=4)(=[O:104])=[O:103])[CH:100]=3)[N:95]=[CH:94][C:93]=2[C:127]([NH2:129])=[O:128])[CH:88]=[CH:89][CH:90]=1>>[OH:70][C@H:69]([C:71]1[CH:80]=[CH:79][C:78]([OH:81])=[C:77]2[C:72]=1[CH:73]=[CH:74][C:75](=[O:82])[NH:76]2)[CH2:68][NH:67][CH:123]([CH3:124])[CH2:122][C:118]1[CH:117]=[C:116]([CH:121]=[CH:120][CH:119]=1)[C:114]([N:112]([CH2:111][C:107]1[CH:106]=[C:105]([S:102]([C:99]2[CH:100]=[C:101]3[C:96](=[C:97]([CH3:126])[CH:98]=2)[N:95]=[CH:94][C:93]([C:127]([NH2:129])=[O:128])=[C:92]3[NH:91][C:87]2[CH:88]=[CH:89][CH:90]=[C:85]([O:84][CH3:83])[CH:86]=2)(=[O:104])=[O:103])[CH:110]=[CH:109][CH:108]=1)[CH3:113])=[O:115]

Participants

Reactant 3

HCID 24996153(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one

HCID 669882814-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[3-(2-oxopropyl)phenylcarbonyl(methyl)amino]methyl]phenyl]sulfonyl]quinoline-3-carboxamide

HCID 86659116(R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 545883126-[[3-[[3-[2-[[(R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]propyl]-N-methylbenzamido]methyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 148, using Intermediate 6 in place of Intermediate 2 and Intermediate 137 in place of Intermediate 112.

Sources & evidence

ORD record: ord-0547ff482ba64bcb90258e8e757089d7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

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