Hydrochloric Acid → 6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine

HRID 2278890Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C)[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)[CH:14]=1.Cl>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)[CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of N-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)acetamide (3.88 g, 12.00 mmol) in THF (30 mL) was treated with 2M HCl (30 mL, 60 mmol), heated at 65° C. for 6 h, cooled to RT and concentrated to dryness. The mixture was treated with H2O, neutralized with solid NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was suspended in 3:2 EtOAc/Hex, sonicated and the resulting solid collected via filtration and dried to afford 6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (3.1 g, 92%) as a white solid. MS (ESI) m/z: 282.1 (M+H+).

Workup

temperaturecooled to RT
concentrationconcentrated to dryness
additionThe mixture was treated with H2O
extractionextracted with EtOAc (2×)
washthe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness
customsonicated
filtrationthe resulting solid collected via filtration
customdried

Sources & evidence

ORD record: ord-94be736b8fbb49a981117443c9a4a916
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

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