1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (1-{4-[8-(1-Methyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037398Notes

Reaction equation

HRID 1037398 reaction equation
C(OC(=O)NC1(C2C=CC(C3C(=O)C4C(=CC(C5NN=CC=5)=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.[C:41]([O:45][C:46](=[O:76])[NH:47][C:48]1([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[C:59](=[O:75])[C:60]4[C:61]([O:67][C:68]=3[C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)=[C:62](Cl)[N:63]=[CH:64][CH:65]=4)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42].[CH3:77][N:78]1[CH:82]=[C:81](B2OC(C)(C)C(C)(C)O2)[CH:80]=[N:79]1>>[C:41]([O:45][C:46](=[O:76])[NH:47][C:48]1([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[C:59](=[O:75])[C:60]4[C:61]([O:67][C:68]=3[C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)=[C:62]([C:81]3[CH:80]=[N:79][N:78]([CH3:77])[CH:82]=3)[N:63]=[CH:64][CH:65]=4)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42]

Participants

4

Reactant 3

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67067641(1-{4-[4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 67067911(1-{4-[8-(1-Methyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterYield 97%

Procedure

Following the procedure used to prepare (1-{-4-[4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester, {1-[4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted with 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole to give the title compound (28.7 mg, 97%). LCMS (Method H): RT=4.04 min, [M+H]+=549.

Sources & evidence

ORD record
ord-ae44383a1ce54720a8d1da67eb88e418
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…