Potassium Carbonate → ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate

HRID 1056154Notes

Reaction equation

HRID 1056154 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[NH:12][C:13]([C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])C)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrCC(C1C=CC=C2C=1N=C(NCC(F)(F)F)C(C)=N2)=O.C(OC(NCC(=O)CC(OCC)=O)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].C(OC(NCC(=O)C(CC(C1C=CC=C2C=1N=C(NCC(F)(F)F)C(C)=N2)=O)C(OCC)=O)=O)(C)(C)C>CN(C=O)C.CCO.CC(O)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:11]1[NH:12][C:13]([C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24]([NH:32][CH2:33][C:34]([F:35])([F:36])[F:37])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 111285644-((tert-Butoxycarbonyl)amino)-3-oxobutanoic acid ethyl esterHCID 897820082-Bromo-1-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)ethanoneHCID 89782299Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoateHCID 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 89783480ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylateYield 55%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

This compound (380 mg, 0.75 mmol, 55% yield) as a yellow solid was prepared according to the procedure described for 293b, using 2-bromo-1-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)ethanone (616) (492 mg, 1.36 mmol), ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate (601) (400 mg, 1.63 mmol) and K2CO3 (0.21 mL, 3.40 mmol) in DMF (2.75 mL), followed by subsequent treatment of the resulting ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate (301a) (530 mg, m/z (ESI, +ve) 527.2 (M+H)+) with NH4OAc (838 mg, 10.87 mmol) in 2 mL of EtOH and AcOH (1 mL) at 60° C. overnight. 1H NMR (400 MHz, CDCl3) δ ppm 7.92-7.98 (m, 1H), 7.68-7.74 (m, 1H), 7.44 (t, J=7.92 Hz, 1H), 7.11 (d, J=2.74 Hz, 1H), 5.44 (br. s., 1H), 5.18 (t, J=6.26 Hz, 1H), 4.56-4.65 (m, 2H), 4.54 (d, J=6.46 Hz, 2H), 4.33 (q, J=7.17 Hz, 2H), 2.63 (s, 3H), 1.35-1.43 (m, 12H). 19F NMR (376 MHz, CDCl3) δ ppm −70.89 (s, 3F). m/z (ESI, +ve) 508.1 (M+H)+.

Sources & evidence

ORD record
ord-0eede458dbc14af98251914c83ca07d3
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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