Methanol → 4-Methoxy-N-(5-(pyrimidin-5-yloxy)pyridin-3-yl)picolinamide

HRID 1045816Notes

Reaction equation

HRID 1045816 reaction equation
F[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([O:17][C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:16]=2)=[O:9])[CH:3]=1.[CH3:24][OH:25]>Cl>[CH3:24][O:25][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([O:17][C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:16]=2)=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 583491834-Fluoro-N-(5-(pyrimidin-5-yloxy)pyridin-3-yl)picolinamide

Product 1

HCID 583491104-Methoxy-N-(5-(pyrimidin-5-yloxy)pyridin-3-yl)picolinamideYield 19%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 8 (30 mg, 0.096 mmol, 1.0 eq) stirred in 1N HCl in MeOH (0.75 mL) at rt overnight. The reaction was concentrated in vacuo and purified by reverse-phase preparatory HPLC to afford 6 mg (19%) of the title compound as a mono-TFA salt: 1H NMR (400 MHz, DMSO-d6) δ 11.05 (s, 1H), 9.09 (s, 1H), 9.03 (d, J=2.0 Hz, 1H), 8.79 (s, 2H), 8.55 (d, J=5.7 Hz, 1H), 8.29 (d, J=2.5 Hz, 1H), 8.14 (t, J=2.3 Hz, 1H), 7.66 (d, J=2.5 Hz, 1H), 7.25 (dd, J=5.7, 2.6 Hz, 1H), 3.93 (s, 3H); ES-MS [M+1]+: 324.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-4c44b7a7e8da481682d94dedf622cf8e
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

Loading…