Pyridinium chloride → 2-[6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-3-pyridyl]-5-dimethylphosphoryl-phenol

HRID 1845846Notes

Reaction equation

HRID 1845846 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:31])=[N:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([P:25]([CH3:28])([CH3:27])=[O:26])=[CH:21][C:20]=2[O:29]C)[CH:18]=1)[CH3:11].Cl.N1C=CC=CC=1>>[NH2:31][C:14]1[N:15]=[CH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([P:25]([CH3:28])([CH3:27])=[O:26])=[CH:21][C:20]=2[OH:29])=[CH:18][C:13]=1[O:12][CH:10]([C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1])[CH3:11]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 601684363-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphoryl-2-methoxy-phenyl)pyridin-2-amine

Product 1

HCID 601686242-[6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-3-pyridyl]-5-dimethylphosphoryl-phenol

Conditions

Temperature
-205 °C

Procedure

A mixture of 3-[1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphoryl-2-methoxy-phenyl)pyridin-2-amine (30 mg) and pyridine HCl salt (0.5 g) was heated to −205° C. for 30 minutes under N2. The reaction mixture was cooled down to room temperature and purified by reverse phase HPLC (water/methanol, 10-100%) as a gummy solid (4 mg); ESMS: m/z 469 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. custompurified by reverse phase HPLC (water/methanol, 10-100%) as a gummy solid (4 mg)

Sources & evidence

ORD record
ord-9989c8157da74452a4e0f0b2b520b6b2
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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