Hydrochloric Acid → HCID 11257045, compound

HRID 2109946Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]([O:19]CC)=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C(O)C.C1COCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:12]([C:17]([OH:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]([C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 3-{[3-tert-butyl-1-(2,6-dimethylphenyl)-1H-pyrazol-5-yl]amino}pyridine-2-carboxylate (2.10 g, 5.35 mmol) in a mixture of ethanol (5 mL) and THF (5 mL) was added lithium hydroxide monohydrate (1.12 mg, 26.8 mmol) in water (10 mL), and the mixture was then heated to 40° C. for 1 h. The reaction mixture was cooled to rt, the pH of the solution was adjusted to 5 by addition of 0.5 N hydrochloric acid, and the mixture was concentrated to dryness. The crude mixture was redissolved in methanol and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 1.65 g (85%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 10.22 (br, s, 1H), 9.52 (s, 1H), 8.03 (dd, 1H), 7.86 (dd, 1H), 7.50 (dd, 1H), 7.30 (dd, 1H), 7.18 (d, 2H), 2.02 (s, 6H), 1.37 (s, 9H); ES-MS m/z 321.3 (MH+); HPLC RT (min.) 2.56.

Workup

temperatureThe reaction mixture was cooled to rt
concentrationthe mixture was concentrated to dryness
dissolutionThe crude mixture was redissolved in methanol
customsubjected to HPLC purification
washa gradient elution from 30% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-22d7518d169240e09ebd7cd0642d8ff2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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