Methylamine → HCID 67531068, compound

HRID 2264595Notes

Reaction equation

HRID 2264595 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:3]=1.[CH3:18][NH2:19]>O>[CH3:18][NH:19][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 574551565-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

Product 1

HCID 67531068HCID 67531068, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolved in 6 ml methylamin solution (2 M in THF), 245 mg (1.0 mMol) 5-(6-chloro-pyrimidin-4-yloxy)-indole (WO 03/099771; Stage 163.1) are stirred for 24 h at rt and 8.5 h at 50° C. The concentrated reaction mixture is dissolved in water and EtOAC, the aqueous layer separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/hexane 1:1→3:1) gives the title compound: MS: [M+1]+=241; TLC(EtOAc): Rf=0.15.

Workup

  1. customThe concentrated reaction mixture
  2. customEtOAC, the aqueous layer separated off
  3. extractionextracted twice with EtOAc
  4. washThe organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af640ddfebbc41f0a7960c663169734e
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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