Potassium Hydroxide → 3-[(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)amino]pyridine-2-carboxamide

HRID 2109954Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]#[N:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([CH3:19])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:20].[K+]>CO>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]([NH2:18])=[O:20])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([CH3:19])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 3-[(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)amino]pyridine-2-carbonitrile (100 mg, 0.39 mmol) in MeOH (1 mL) was added an aqueous solution of KOH (3 M, 1 mL), and the mixture was stirred at 40° C. for 48 h. The organic solvent was removed under reduced pressure, and the aqueous layer was acidified to pH 1 to 2 with 1 N aqueous HCl. The mixture was extracted with ethyl acetate (3×). After removal of the solvent under reduced pressure, the crude residue was subjected to preparative HPLC purification with a gradient elution from 20% to 90% acetonitrile in water to give the above product as an oil (6.2 mg, 6%). 1H NMR (400 MHz, CD3OD) δ 1.35 (s, 9H), 3.72 (s, 3H), 6.80 (s, 1H), 7.39-7.42 (m, 2H), 8.08-8.11 (m, 1H). ES-MS m/z 274.1 (MH+), HPLC RT (min) 1.47.

Workup

customThe organic solvent was removed under reduced pressure
extractionThe mixture was extracted with ethyl acetate (3×)
customAfter removal of the solvent under reduced pressure
customthe crude residue was subjected to preparative HPLC purification with a gradient elution from 20% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-9cf71214fad745ee9ca8ab3950f6421c
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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