Hydrochloric Acid → 4-(8-(3-(Trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoic acid

HRID 1913093Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl>[OH-].[Na+].O1CCOCC1>[F:29][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 4-(8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino)benzoate (1.03 g, 2.50 mmol, 1 equiv) in 2M aqueous sodium hydroxide (10 mL) and 1,4-dioxane (5 mL) was heated at 80-90° C. After 3 h, the solution was cooled to 0° C. and neutralized by the addition of 6M HCl until pH=4-5. The resulting solid was collected by filtration and rinsed sequentially with water, isopropanol, and hexanes to afford crude 4-(8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoic acid (1.0 g, HPLC purity: 89%). LCMS (ESI) m/z: 398.9; 1H NMR (400 MHz, DMSO-d6) δ: 12.45 (br s, 1 H), 10.22 (s, 1 H), 8.89 (d, J=6.8 Hz, 1 H), 8.65 (s, 1 H), 8.42 (d, J=6.9 Hz, 1 H), 8.03 (m, 1 H), 7.77-7.84 (m, 6 H), 7.21 (t, J=7.0 Hz, 1 H).

Workup

filtrationThe resulting solid was collected by filtration
washrinsed sequentially with water, isopropanol, and hexanes

Sources & evidence

ORD record: ord-f7cf32152f65479cabfef79836bed8cc
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609687B2

Reaction notes

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