Hydrochloric Acid → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoic acid

HRID 915587Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>CO.C1COCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate (Example 235, 115 mg, 0.29 mmol) in a mixture of methanol (1 mL) and THF (1 mL) was added lithium hydroxide monohydrate (123 mg, 2.94 mmol) in water (2 mL), and the mixture was heated to 40° C. for 1 h. The reaction mixture was then cooled to rt, and the pH of the solution was adjusted to 5 using 0.5 N aq HCl. The solvent was removed under reduced pressure, and the residue was subjected to HPLC purification using gradient elution from 10% to 90% acetonitrile in water to afford 109.6 mg (99%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.28 (s, 1H), 7.76 (s, 1H), 7.26-7.37 (m, 6H), 6.15 (s, 1H), 2.60 (q, 2H), 2.08 (s, 3H), 1.37 (s, 9H), 1.23 (t, 3H). ES-MS m/z 378.3 (MH+); HPLC RT (min) 3.64.

Workup

temperatureThe reaction mixture was then cooled to rt
customThe solvent was removed under reduced pressure
customthe residue was subjected to HPLC purification
washelution from 10% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-5c7eafa6709c4256889b6c71f7f3076b
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265144B2

Reaction notes

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