Ethyl Acetate → HCID 20826922, compound

HRID 495458Notes

Reaction equation

HRID 495458 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]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]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]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]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 20826881HCID 20826881, compound

Product 1

HCID 20826922HCID 20826922, 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-(6-quinolinyl)-2,4-pyrimidinediamine (Example 111, 150 mg, 0.353 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 light yellow 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-d6b107e0c56445ab9aab9f5a1d5ab4d8
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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