Hydrochloric Acid → HCID 11772917, compound

HRID 2109941Notes

Reaction equation

[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][C:4]1[CH:8]=[C:7]([NH:9][C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([O:14]CC)=[O:13])[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[N:5]=1.O.[OH-].[Li+].Cl>C(O)C.C1COCC1.O>[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][C:4]1[CH:8]=[C:7]([NH:9][C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([OH:14])=[O:13])[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[N:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 2-{[3-(2,2-dimethylpropyl)-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}nicotinate (266 mg, 0.68 mmol) (step 1) in a mixture of ethanol (1 mL) and THF (1 mL) was added lithium hydroxide monohydrate (284 mg, 6.8 mmol) in water (2 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 solution, and was concentrated to dryness. The crude product was redissolved in methanol and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 240 mg (97%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 10.39 (s, 1H), 8.43 (dd, 1H), 8.14 (dd, 1H), 7.25-7.42 (m, 4H), 6.81-6.86 (m, 2H), 2.57 (s, 2H), 2.05 (s, 3H), 1.00 (s, 9H); ES-MS m/z 365.3 (MH+); HPLC RT (min) 3.67.

Workup

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

Sources & evidence

ORD record: ord-27bf07e1e8d7417fade688bd64130894
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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