Sodium Carbonate → HCID 59346505, compound

HRID 535369Notes

Reaction equation

HRID 535369 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][N:8]2[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.Cl[C:17]1[C:18]2[CH2:26][N:25]([C:27]3[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=3)[CH2:24][CH2:23][C:19]=2[N:20]=[CH:21][N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[Cl:33][C:32]1[C:27]([N:25]2[CH2:24][CH2:23][C:19]3[N:20]=[CH:21][N:22]=[C:17]([NH:1][C:2]4[CH:10]=[C:9]5[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][N:8]5[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=4)[C:18]=3[CH2:26]2)=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 218651761-(6-Amino-3,3-dimethylindolin-1-yl)ethanoneHCID 59346527HCID 59346527, compound

Product 1

HCID 59346505HCID 59346505, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(6-amino-3,3-dimethylindolin-1-yl)ethanone (80 mg), 4-chloro-6-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (80 mg), and CH3CN (5 mL) was run in a Microwave Reactor at 180° C. for 1 h. After cooling, the mixture was treated with sat. aq. Na2CO3 and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column to give a light yellow solid (75 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column

Sources & evidence

ORD record
ord-83e1ef22f7464124bbd3f84924f0afbf
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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