(R)-6-((3-((4'-(4-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)butyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide → (R)-6-((3-((4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)pent-1-yn-1-yl)-2-methylphenyl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944967Notes

Reaction equation

[Si:1]([O:8][C@H:9]([C:63]1[C:68]2[O:69][CH2:70][C:71](=[O:73])[NH:72][C:67]=2[C:66]([OH:74])=[CH:65][CH:64]=1)[CH2:10][NH:11][CH2:12][CH2:13]CCC1C=CC(C2C=CC(NC(C3C=C(S(C4C=C5C(=C(C)C=4)N=CC(C(N)=O)=C5NC4C=CC=C(OC)C=4)(=O)=O)C=CC=3)=O)=CC=2)=CC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:75][O:76][C:77]1[CH:78]=[C:79]([NH:83][C:84]2[C:93]3[C:88](=[C:89]([CH3:119])[CH:90]=[C:91]([S:94]([C:97]4[CH:102]=[CH:101][CH:100]=[C:99]([C:103](=[O:118])[NH:104][C:105]5[CH:110]=[CH:109][C:108]([C:111]#[C:112][CH2:113]CC=O)=[CH:107][C:106]=5[CH3:117])[CH:98]=4)(=[O:96])=[O:95])[CH:92]=3)[N:87]=[CH:86][C:85]=2[C:120]([NH2:122])=[O:121])[CH:80]=[CH:81][CH:82]=1>>[Si:1]([O:8][C@H:9]([C:63]1[C:68]2[O:69][CH2:70][C:71](=[O:73])[NH:72][C:67]=2[C:66]([OH:74])=[CH:65][CH:64]=1)[CH2:10][NH:11][CH2:12][CH2:13][CH2:113][C:112]#[C:111][C:108]1[CH:109]=[CH:110][C:105]([NH:104][C:103]([C:99]2[CH:98]=[C:97]([S:94]([C:91]3[CH:92]=[C:93]4[C:88](=[C:89]([CH3:119])[CH:90]=3)[N:87]=[CH:86][C:85]([C:120]([NH2:122])=[O:121])=[C:84]4[NH:83][C:79]3[CH:80]=[CH:81][CH:82]=[C:77]([O:76][CH3:75])[CH:78]=3)(=[O:95])=[O:96])[CH:102]=[CH:101][CH:100]=2)=[O:118])=[C:106]([CH3:117])[CH:107]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 86659117(R)-6-((3-((4'-(4-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)butyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HCID 866591194-((3-Methoxyphenyl)amino)-8-methyl-6-((3-((2-methyl-4-(5-oxopent-1-yn-1-yl)phenyl)carbamoyl)phenyl)sulfonyl)quinoline-3-carboxamide

Product 1

HCID 86659125(R)-6-((3-((4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)pent-1-yn-1-yl)-2-methylphenyl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

Procedure

The title compound was synthesized in a manner analogous to that described in Intermediate 151, using Intermediate 117 in place of Intermediate 124. ES/MS calcd. for C53H58N6O9SSi 982.4. Found m/z=983 (M+H)+.

Sources & evidence

ORD record: ord-b06fe899809f434aac7a2113b17e7da9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

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