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

HRID 1056152Notes

Reaction equation

HRID 1056152 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][C@H:67]([CH3:76])[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.CC(O)=O>[C:59]([O:63][C:64]([NH:66][CH:67]([CH3:76])[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

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11288402Ethyl (4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-oxopentanoateHCID 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 89782241Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxopentanoateYield 66%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

This compound (245 mg, 46% yield) as a yellow foam was prepared according to the procedures described for 293b, using 2-bromo-1-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanone (605) (366 mg, 1.03 mmol), (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate (602) (322 mg, 1.24 mmol) and K2CO3 (357 mg, 2.58 mmol) in DMF (3.5 mL), 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-oxopentanoate (297a) (360 mg, 0.68 mmol, 65% yield, m/z 533.2 (ESI, +ve) (M+H)+) with NH4OAc (637 mg, 8.27 mmol) in 2 mL of EtOH and AcOH (1 mL). 1H NMR (400 MHz, CDCl3) δ ppm 7.61 (dd, J=9.00, 5.67 Hz, 1H), 7.32-7.36 (m, 1H), 7.20 (dd, J=11.54, 9.00 Hz, 1H), 6.97 (d, J=9.98 Hz, 1H), 5.09-5.21 (m, 1H), 4.96 (s, 1H), 4.36 (qd, J=7.14, 2.05 Hz, 2H), 2.54 (s, 3H), 1.72 (s, 9H), 1.53 (d, J=6.85 Hz, 3H), 1.36-1.46 (m, 12H). 19F NMR (376 MHz, CDCl3) δ ppm −107.07 (s, 1F). m/z 514.2 (ESI, +ve) (M+H)+.

Sources & evidence

ORD record
ord-9d8435eb69bb448a82eeb642d4918d70
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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