Ethyl 3-(1-{[(tert-butoxy)carbonyl]amino}cyclopropyl)-3-oxopropanoate → ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

HRID 1056198Notes

Reaction equation

HRID 1056198 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]2[NH:13]C(C3C=CC=C4C=3N=C(NC(C)(C)C)C(C)=N4)=C[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:39][C:40]([C:42]1[CH:51]=[CH:50][CH:49]=[C:48]2[C:43]=1[N:44]=[C:45]([NH:53][CH2:54][CH:55]([F:57])[F:56])[C:46]([CH3:52])=[N:47]2)=O.C(OC(NC1(C(=O)CC(OCC)=O)CC1)=O)(C)(C)C>CCO.CC(O)=O>[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]2[NH:13][C:40]([C:42]3[CH:51]=[CH:50][CH:49]=[C:48]4[C:43]=3[N:44]=[C:45]([NH:53][CH2:54][CH:55]([F:57])[F:56])[C:46]([CH3:52])=[N:47]4)=[CH:39][C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 89781999Ethyl 3-(1-{[(tert-butoxy)carbonyl]amino}cyclopropyl)-3-oxopropanoateHCID 897820242-Bromo-1-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)ethanoneHCID 89783651ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 89783739ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-((2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylateYield 41%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

This compound (0.40 g, 41% yield) as a yellow amorphous solid was prepared according to the procedures described for Intermediate 324b, using 2-bromo-1-(34(2,2-difluoroethyl)amino)-2-methylquinoxalin-5-yl)ethanone (617) (583 mg, 2.26 mmol), ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-3-oxopropanoate (604) (650 mg, 1.89 mmol) as the starting materials, followed by the subsequent treatment of the resulting 331a (m/z (ESI, +ve) 535.2 (M+H)+) with NH4OAc (728 mg, 9.44 mmol) in 3 mL of EtOH and 1.5 mL of HOAc at 50° C. for 4 h. m/z (ESI, +ve) 516.2 (M+H)+.

Sources & evidence

ORD record
ord-1998e06e2a0041fcb889cfc74fec865a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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