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

HRID 1056239Notes

Reaction equation

HRID 1056239 reaction equation
C(OC[CH:10]([C:19]1[NH:20][C:21]([C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[N:31]=[C:32]([NH:40][C:41]2(C)[CH2:43][CH2:42]2)[C:33]([CH3:39])=[N:34]3)=[CH:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.C(OC(NCC(=O)CC([O-])=O)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].BrCC(C1C(F)=CC=C2C=1N=C(NC1CC1)C(C)=N2)=O.C(OC(NCC(=O)C(CC(C1C=CC=C2C=1N=C(NC1CC1)C(C)=N2)=O)C(OCC)=O)=O)(C)(C)C>CN(C=O)C.CCO.CC(O)=O>[C:15]([O:14][C:12]([NH:11][CH2:10][C:19]1[NH:20][C:21]([C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[N:31]=[C:32]([NH:40][CH:41]2[CH2:42][CH2:43]2)[C:33]([CH3:39])=[N:34]3)=[CH:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:13])([CH3:16])([CH3:17])[CH3:18]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 89782079Ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoateHCID 897821632-Bromo-1-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanoneHCID 89783850ethyl 2-(2-(benzyloxy)-1-((tert-butoxycarbonyl)amino)ethyl)-5-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylateHCID 1317364244-((Tert-butoxycarbonyl)amino)-3-oxobutanoate

Product 1

HCID 89783568ethyl 2-(((tert-butoxycarbonyl)amino)methyl)-5-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylateYield 35%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

This compound (0.25 g, 35% yield) as a yellow solid was prepared according to the procedures described for Intermediate 355b, using 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate (601) (0.45 g, 1.84 mmol), K2CO3 (0.53 g, 3.83 mmol), 2-bromo-1-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)ethanone (613) (0.49 g, 1.53 mmol) in DMF (4 mL) as starting material, followed by subsequent treatment of ethyl 4-((tert-butoxycarbonyl)amino)-2-(2-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-3-oxobutanoate (363a: m/z (ESI, +ve) 485.1 (M+H)+) with NH4OAc (0.36 g, 4.6 mmol) in EtOH (6 mL) and AcOH (1.5 mL). 1H NMR (400 MHz, DMSO-d6) δ 12.56 (br. s., 1H), 7.60 (dd, J=0.98, 8.02 Hz, 1H), 7.54 (d, J=1.96 Hz, 1H), 7.31-7.39 (m, 2H), 7.06 (br. s., 1H), 4.50 (d, J=5.48 Hz, 2H), 4.22 (q, J=7.04 Hz, 2H), 3.03 (br. s., 1H), 2.49 (s, 3H), 1.38 (s, 9H), 1.30 (t, J=7.04 Hz, 3H), 0.96-1.02 (m, 2H), 0.62-0.69 (m, 2H). m/z (ESI, +ve) 466.2 (M+H)+.

Sources & evidence

ORD record
ord-d59e9043ab9f426abedb30baa8248cd6
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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