Water → HCID 58942264, compound

HRID 2092318Notes

Reaction equation

HRID 2092318 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].Cl[C:14]1[C:23]2[C:18](=[C:19]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]=[C:30]([NH:35][CH3:36])[N:29]=[CH:28]4)[C:20]([CH3:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:7][C:14]1[C:23]2[C:18](=[C:19]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]=[C:30]([NH:35][CH3:36])[N:29]=[CH:28]4)[C:20]([CH3:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 79832VeratrylamineHCID 58942249HCID 58942249, compound

Product 1

HCID 58942264HCID 58942264, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Dissolved 3,4-dimethoxybenzylamine (3.04 ml, 20.2 mmol) in NMP (15.0 mL) and added 6-(1-chloro-6-methylisoquinolin-5-yl)-N-methylquinazolin-2-amine (2.25 g, 6.72 mmol) as a solid in a sealed vessel and heated the reaction to 220° C. in the microwave 20 minutes. Dripped the reaction mixture into water and isolated the resulting precipitate. Air-dried the solid and redissolved in 2M NH3/MeOH. Concentrated in vacuo, redissolved wet slurry in EtOAc and dried the slurry over Na2SO4. Concentrated and loaded the crude material on a column, and purified the crude eluting with 20-100% EtOAc/hexanes. The pure fractions were combined and concentrated to afford 6-(1-(3,4-dimethoxybenzylamino)-6-methylisoquinolin-5-yl)-N-methylquinazolin-2-amine. MS (M+H)+ 466.

Workup

  1. temperatureheated
  2. customthe reaction to 220° C. in the microwave 20 minutes
  3. customisolated the resulting precipitate
  4. customAir-dried the solid
  5. dissolutionredissolved in 2M NH3/MeOH
  6. concentrationConcentrated in vacuo
  7. dissolutionredissolved wet slurry in EtOAc
  8. dry with materialdried the slurry over Na2SO4
  9. concentrationConcentrated
  10. custompurified the crude
  11. washeluting with 20-100% EtOAc/hexanes
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8d17fc7780874bbb9ade1a5e219ed85b
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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