Potassium Carbonate → 3-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-[1-[1-(dimethylphosphorylmethyl)-4-piperidyl]pyrazol-4-yl]pyridin-2-amine

HRID 1845833Notes

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]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11].Cl[CH2:32][P:33](=[O:36])([CH3:35])[CH3:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[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]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH2:32][P:33]([CH3:35])([CH3:34])=[O:36])[CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(1-(2,6-dichloro-3-fluoro-phenyl)ethoxy)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-amine (6 mg, 0.013 mmol), chloromethyl-dimethyl-phosphine oxide (100 mg, 0.79 mmol), and potassium carbonate (0.2 g) in DMF (5 mL) was heated to 80° C. overnight. The solid was removed and the residue was purified by HPLC (water/methanol, 10˜100%) to give the title compound as an off-white solid (3 mg, 40%); ESMS: m/z 540 (M+H)+.

Workup

customThe solid was removed
customthe residue was purified by HPLC (water/methanol, 10˜100%)

Sources & evidence

ORD record: ord-188980481cbd49d096a9d12626c2098b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951993B2

Reaction notes

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