4-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[4-(5-oxopent-1-yn-1-yl)phenyl]carbamoyl]phenyl]sulfonyl]quinoline-3-carboxamide → (R)-6-[[3-[[4-[5-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pent-1-ynyl]-phenyl]carbamoyl]phenyl]-sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944959Notes

Reaction equation

[Si:1]([O:8][C@H:9]([C:55]1[CH:64]=[CH:63][C:62]([OH:65])=[C:61]2[C:56]=1[CH:57]=[CH:58][C:59](=[O:66])[NH:60]2)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CCCNC(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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:67][O:68][C:69]1[CH:70]=[C:71]([NH:75][C:76]2[C:85]3[C:80](=[C:81]([CH3:110])[CH:82]=[C:83]([S:86]([C:89]4[CH:94]=[CH:93][CH:92]=[C:91]([C:95](=[O:109])[NH:96][C:97]5[CH:102]=[CH:101][C:100](C#CCCC=O)=[CH:99][CH:98]=5)[CH:90]=4)(=[O:88])=[O:87])[CH:84]=3)[N:79]=[CH:78][C:77]=2[C:111]([NH2:113])=[O:112])[CH:72]=[CH:73][CH:74]=1>>[Si:1]([O:8][C@H:9]([C:55]1[CH:64]=[CH:63][C:62]([OH:65])=[C:61]2[C:56]=1[CH:57]=[CH:58][C:59](=[O:66])[NH:60]2)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:100]1[CH:101]=[CH:102][C:97]([NH:96][C:95]([C:91]2[CH:90]=[C:89]([S:86]([C:83]3[CH:84]=[C:85]4[C:80](=[C:81]([CH3:110])[CH:82]=3)[N:79]=[CH:78][C:77]([C:111]([NH2:113])=[O:112])=[C:76]4[NH:75][C:71]3[CH:72]=[CH:73][CH:74]=[C:69]([O:68][CH3:67])[CH:70]=3)(=[O:88])=[O:87])[CH:94]=[CH:93][CH:92]=2)=[O:109])=[CH:98][CH:99]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 585051794-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[4-(5-oxopent-1-yn-1-yl)phenyl]carbamoyl]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 58505204(R)-6-[[3-[[4-[5-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pent-1-ynyl]-phenyl]carbamoyl]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 115 in place of Intermediate 112. ES/MS calcd. for C53H57N6O8SSi+ 965.4. Found m/z=965.4 (M+H)+.

Sources & evidence

ORD record: ord-a4f114a566e9438c8c3a8afaa71022a0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

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