Hydrochloric Acid → Methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate

HRID 1056292Notes

Reaction equation

HRID 1056292 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([CH3:15])=[N:10]2)=[O:4].[CH:21]1([C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[C:17]([NH:16][C:8]1[C:9]([CH3:15])=[N:10][C:11]2[C:6]([N:7]=1)=[C:5]([C:3](=[O:4])[CH2:2][CH:25]([C:24]([CH:21]1[CH2:23][CH2:22]1)=[O:30])[C:26]([O:28][CH3:29])=[O:27])[CH:14]=[CH:13][CH:12]=2)([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 897821422-Bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone

Product 1

HCID 89782054Methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone (606) (0.27 g, 0.803 mmol), methyl 3-cyclopropyl-3-oxopropanoate (Accela ChemBio, 0.114 mL, 0.803 mmol), K2CO3 (EMD, 0.333 g, 2.409 mmol), in DMF (3.21 ml) was combined and stirred overnight at RT. Reaction mixture was diluted with DCM and water. The aqueous layer was acidified with 1 N HCl solution and back extracted with DCM. The organic layers were combined and washed with water and brine to remove DMF. Volatile solvents were removed by rotovap. The product methyl 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-(cyclopropanecarbonyl)-4-oxobutanoate (418a) was advanced to next step. m/z (ESI, +ve) 398.1 (M+H).

Workup

  1. customReaction mixture
  2. extractionback extracted with DCM
  3. washwashed with water and brine
  4. customto remove DMF
  5. customVolatile solvents were removed by rotovap

Sources & evidence

ORD record
ord-67e89136baae4291b4bc2e6ffd253075
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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