Ethyl Acetate → HCID 20826920, compound

HRID 495459Notes

Reaction equation

HRID 495459 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[N:15]=3)[CH:11]=2)[C:6]([CH3:34])([CH3:33])[CH2:5]1)(=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>CCO.Cl>[CH3:33][C:6]1([CH3:34])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[N:15]=3)=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 20826880HCID 20826880, compound

Product 1

HCID 20826920HCID 20826920, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of N4-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-N2-(3,4,5-tris(methoxy)phenyl)-2,4-pyrimidinediamine (Example 114, 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 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 provide the desired product as a purple solid. M+H—422; Calc'd for C23H27N5O3—421.

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 was purified via medium pressure liquid chromatography

Sources & evidence

ORD record
ord-4806c553ec9c40d09797ecd2b2d93fcf
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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