Methylamine → HCID 59394609, compound

HRID 1971404Notes

Reaction equation

HRID 1971404 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([CH2:18]OS(C)(=O)=O)[CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:24])[NH:6]2.[CH3:25][NH2:26].C1COCC1>C(Cl)Cl.O.CCOC(C)=O>[F:1][C:2]1[C:10]([O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([CH2:18][NH:26][CH3:25])[CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:24])[NH:6]2

Participants

7

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 59394089Methanesulfonic acid 6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl ester

Product 1

HCID 59394609HCID 59394609, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid 6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl ester (2.5 g, 8.78 mmol) is stirred in DCM (40.0 mL) with 1 M methylamine in THF (4.39 mL, 8.78 mmol) at rt for 24 h. The reaction is diluted with H2O and EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and purified by FCC eluting with first 10-100% EtOAc in heptanes, then washing with 0-25% MeOH with NH3 in EtOAc to provide the title compound. MS (ESI) m/z 287.2 (M+1); 1H NMR (400 MHz, MeOD) δ ppm 8.63 (d, J=1.01 Hz, 1 H) 7.11 (d, J=8.59 Hz, 1 H) 7.02 (s, 1 H) 6.85 (dd, J=8.59, 7.33 Hz, 1 H) 6.23 (s, 1 H) 3.81 (s, 2 H) 2.41 (s, 3 H) 2.44 (s, 3 H).

Workup

  1. washThe organic layer is washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. custompurified by FCC
  5. washeluting with first 10-100% EtOAc in heptanes
  6. washwashing with 0-25% MeOH with NH3 in EtOAc

Sources & evidence

ORD record
ord-d8df286170db4fa6a8918120e116e068
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

Loading…