Potassium Carbonate → Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate

HRID 1056151Notes

Reaction equation

HRID 1056151 reaction equation
C(OC(NC(C1NC(C2C=CC=C3C=2N=C(NCC(F)(F)F)C(C)=N3)=CC=1C(OCC)=O)C)=O)(C)(C)C.Br[CH2:39][C:40]([C:42]1[C:51]([F:52])=[CH:50][CH:49]=[C:48]2[C:43]=1[N:44]=[C:45]([NH:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:46]([CH3:53])=[N:47]2)=[O:41].[C:59]([O:63][C:64]([NH:66][CH2:67][C:68](=[O:75])[CH2:69][C:70]([O:72][CH2:73][CH3:74])=[O:71])=[O:65])([CH3:62])([CH3:61])[CH3:60].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCO>[C:59]([O:63][C:64]([NH:66][CH2:67][C:68](=[O:75])[CH:69]([CH2:39][C:40]([C:42]1[C:51]([F:52])=[CH:50][CH:49]=[C:48]2[C:43]=1[N:44]=[C:45]([NH:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:46]([CH3:53])=[N:47]2)=[O:41])[C:70]([O:72][CH2:73][CH3:74])=[O:71])=[O:65])([CH3:61])([CH3:62])[CH3:60]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 111285644-((tert-Butoxycarbonyl)amino)-3-oxobutanoic acid ethyl esterHCID 897819262-Bromo-1-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanoneHCID 89783413ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 89782097Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoateYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

This compound (873 mg, 34% yield) as a yellow foam was prepared according to the procedure described for intermediate 293b, using 2-bromo-1-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanone (605) (1.81 g, 5.11 mmol), ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate (601) (1.50 g, 6.13 mmol) and K2CO3 (1.77 g, 12.77 mmol) in DMF (17 mL) was stirred at RT for 6 h, followed by the subsequent treatment of the resulting ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate (296a) (1.43 g, 2.76 mmol, 54% yield, m/z (ESI, +ve) 519.2 (M+H)+) with NH4Oac (3.15 g, 40.9 mmol) in 12 mL of EtOH and AcOH (6 mL). 1H NMR (400 MHz, CDCl3) δ ppm 7.63 (dd, J=8.80, 5.67 Hz, 1H), 7.34 (dd, J=4.60, 2.45 Hz, 1H), 7.21 (dd, J=11.64, 8.90 Hz, 1H), 4.94 (s, 1H), 4.62 (d, J=5.87 Hz, 2H), 4.34 (q, J=7.24 Hz, 2H), 2.54 (s, 3H), 1.69 (s, 9H), 1.43 (s, 9H), 1.38-1.42 (m, 3H). 19F NMR (376 MHz, CDCl3) δ ppm −107.37 (s, 1F). m/z (ESI, +ve) 500.1 (M+H)+.

Sources & evidence

ORD record
ord-dd7dc8ce42014191ada261cdb31f27f0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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