Potassium Carbonate → Methyl 2-(2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-4,4-dimethoxy-3-oxopentanoate

HRID 1056287Notes

Reaction equation

HRID 1056287 reaction equation
[CH3:1][O:2][C:3]([O:12][CH3:13])([CH3:11])[C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]([C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[N:26]=[C:27]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:28]([CH3:34])=[N:29]2)=[O:23]>CN(C=O)C.C(Cl)Cl>[C:36]([NH:35][C:27]1[C:28]([CH3:34])=[N:29][C:30]2[C:25]([N:26]=1)=[C:24]([C:22](=[O:23])[CH2:21][CH:5]([C:4](=[O:10])[C:3]([O:2][CH3:1])([O:12][CH3:13])[CH3:11])[C:6]([O:8][CH3:9])=[O:7])[CH:33]=[CH:32][CH:31]=2)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5076552Methyl 4,4-dimethoxy-3-oxopentanoateHCID 897821422-Bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone

Product 1

HCID 89781933Methyl 2-(2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-oxoethyl)-4,4-dimethoxy-3-oxopentanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4,4-dimethoxy-3-oxovalerate (Sigma Aldrich, 0.127 ml, 0.744 mmol), K2CO3 (EMD Biosciences, 0.135 ml, 2.231 mmol), 2-bromo-1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone (606) (0.25 g, 0.744 mmol) in DMF (2.97 mL) was stirred at RT for 2 d. Reaction mixture was diluted with DCM and washed with alternating water and brine washes (2×) to remove DMF. The organic layer was concentrated and advanced to the next step. m/z (ESI, +ve) 446.1 (M+H).

Workup

  1. customReaction mixture
  2. washwashed with alternating water and brine washes (2×)
  3. customto remove DMF
  4. concentrationThe organic layer was concentrated and advanced to the next step

Sources & evidence

ORD record
ord-4e5992c647834d4a8b32139a9df6641b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…