Ethyl Acetate → HCID 20826921, compound

HRID 495457Notes

Reaction equation

HRID 495457 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]3[N:19]=[C:18]([NH:20][C:21]4[CH:22]=[N:23][C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:17]=[CH:16][N:15]=3)[CH:11]=2)[C:6]([CH3:32])([CH3:31])[CH2:5]1)(=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>CCO.Cl>[CH3:31][C:6]1([CH3:32])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([NH:20][C:21]4[CH:22]=[N:23][C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10159390HCID 10159390, compound

Product 1

HCID 20826921HCID 20826921, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of N2-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-N4-(3-quinolinyl)-2,4-pyrimidinediamine (Example 110, 170 mg, 0.266 mmol) was dissolved in EtOH (6 mL) and 10 drops conc. HCl were added. The mixture was heated to reflux in a sealed tube for 72 h. The crude mixture was poured into EtOAc (125 mL) and sat NaHCO3 (20 mL). The organics were dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified via medium pressure liquid chromatography using linear gradient starting from 0:100 MeOH/CH2Cl2 ending with 10:90 MeOH/CH2Cl2 as the solvent system to yield the desired product as a tan solid. M+H—383; Calc'd for C23H22N6—382.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux in a sealed tube for 72 h
  3. dry with materialThe organics were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified via medium pressure liquid chromatography

Sources & evidence

ORD record
ord-83435de859f5448eb4076fd8e0656a19
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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