Ethyl 3-(1-{[(tert-butoxy)carbonyl]amino}cyclopropyl)-3-oxopropanoate → ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(6-fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]2[NH:13][C:14]([C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[N:24]=[C:25]([NH:33][C:34]([CH3:37])(C)[CH3:35])[C:26]([CH3:32])=[N:27]4)=[CH:15][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].BrCC(C1C([F:52])=CC=C2C=1N=C(NC(C)C)C(C)=N2)=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:14]([C:22]3[C:31]([F:52])=[CH:30][CH:29]=[C:28]4[C:23]=3[N:24]=[C:25]([NH:33][CH:34]([CH3:37])[CH3:35])[C:26]([CH3:32])=[N:27]4)=[CH:15][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-oxopropanoate
HCID 897820862-Bromo-1-(6-fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)ethanone
HCID 89783651ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylateProduct 1
Reagents, catalysts & solvents 2
Procedure
This compound (1.07 g, 85% yield) as a yellow amorphous solid was prepared according to the procedures described for Intermediate 324b, using 2-bromo-1-(6-fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)ethanone (619) (840 mg, 2.47 mmol), ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-3-oxopropanoate (604) (804 mg, 2.96 mmol) as the starting materials, followed by the subsequent treatment of the resulting 330a (m/z (ESI, +ve) 531.2 (M+H)+) with NH4OAc (952 mg, 12.35 mmol) in 3 mL of EtOH and 1.5 mL of HOAc at 50° C. for 4 h. m/z (ESI, +ve) 512.2 (M+H)+.
Sources & evidence
- ORD record
- ord-b61d6964bf2e4d28b6e4572c6ea0de23
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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