Potassium Carbonate → ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

HRID 1056263Notes

Reaction equation

HRID 1056263 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)([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])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].BrCC(C1C=CC=C2C=1N=C(NCC(F)F)C(C)=N2)=O.C(OC(N[C@H](C)C(=O)CC(OCC)=O)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCO.CC(O)=O>[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][CH:34]([F:35])[F:36])[C:25]([CH3:31])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:10])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11288402Ethyl (4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-oxopentanoateHCID 897820242-Bromo-1-(3-((2,2-difluoroethyl)amino)-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 89783848ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylateYield 82%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

This compound (950 mg, 82% yield) as yellow crystalline solid was prepared according to the procedure described for Intermediate 293b, using 2-bromo-1-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)ethanone (617) (790 mg, 2.295 mmol), (R)-ethyl 4-((tert-butoxycarbonyl)amino)-3-oxopentanoate (602) (714 mg, 2.75 mmol) and K2CO3 (793 mg, 5.74 mmol) in DMF (7.0 mL) as the starting material, followed by the treatment of the resulting 4-ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxopentanoate (1.03 g, m/z (ESI, +ve ion) 523.1 (M+H)+) with NH4OAc (1.42 g, 18.36 mmol) in EtOH (6 mL) and AcOH (2 mL). 19F NMR (376 MHz, CDCl3) δ ppm −122.78 (1F, s), −123.02 (1F, s). m/z (ESI, +ve ion) 504.1 (M+H)+.

Sources & evidence

ORD record
ord-a9d409fe68f74816b8e515d4f72ab860
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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