1-(4-(5-bromopent-1-yn-1-yl)phenyl)-3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)urea → (R)-tert-butyl (2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)(6-(4-(4-(3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)ureido)phenyl)butoxy)hexyl)carbamate

HRID 385281Notes

Reaction equation

BrCCCC#CC1C=C[C:10]([NH:13][C:14]([NH:16][CH2:17][C:18]2[C:19]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:20]3[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:21]3=[N:22][C:23]=2[CH2:24][CH3:25])=[O:15])=[CH:9]C=1.NC1C=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][N:56]([CH2:64][C@@H:65]([C:74]2[CH:83]=[CH:82][C:81]([O:84][C:85]([O:87][C:88]([CH3:91])([CH3:90])[CH3:89])=[O:86])=[C:80]3[C:75]=2[CH:76]=[CH:77][C:78]([O:92][C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])=[N:79]3)[O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[CH:41][CH:40]=1>>[C:96]([O:95][C:93]([O:92][C:78]1[CH:77]=[CH:76][C:75]2[C:80](=[C:81]([O:84][C:85]([O:87][C:88]([CH3:91])([CH3:90])[CH3:89])=[O:86])[CH:82]=[CH:83][C:74]=2[C@@H:65]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[CH2:64][N:56]([CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][O:49][CH2:48][CH2:47][CH2:46][CH2:45][C:42]2[CH:41]=[CH:40][C:10]([NH:13][C:14]([NH:16][CH2:17][C:18]3[C:19]([NH:31][CH:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[C:20]4[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:21]4=[N:22][C:23]=3[CH2:24][CH3:25])=[O:15])=[CH:9][CH:43]=2)[C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[N:79]=1)=[O:94])([CH3:97])([CH3:98])[CH3:99]

Participants

Reactant 2

HCID 585052951-(4-(5-bromopent-1-yn-1-yl)phenyl)-3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)urea

HCID 66989909(R)-tert-butyl (6-(4-(4-aminophenyl)butoxy)hexyl)(2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate

Product 1

HCID 86659067(R)-tert-butyl (2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)(6-(4-(4-(3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)ureido)phenyl)butoxy)hexyl)carbamate

Procedure

The title compound was prepared in a manner analogous to that described for Intermediate 35, using Intermediate 42 in place of Intermediate 24. ES/MS calcd. for C65H99N8O12Si+ 1211.7. found m/z=1211.6 (M+H)+.

Sources & evidence

ORD record: ord-77de730316c143f7aa05722a8a22a8de
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367829B2

Reaction notes

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