Hydrochloric Acid → [5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

HRID 1971590Notes

Reaction equation

C([N:8]1[CH:12]=[C:11]([C:13]2[N:18]3[N:19]=[C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:25][CH:24]=4)[N:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[NH:9]1[CH:10]=[C:11]([C:13]2[N:18]3[N:19]=[C:20]([NH:22][C:23]4[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:27][CH:28]=4)[N:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)[CH:12]=[N:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

[5-(1-Benzyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (1.66 g, 3.46 mmol) and palladium hydroxide (1.6 g) were suspended in methanol (50 mL) and conc. HCl (1 mL) added. The suspension was then stirred under an atmosphere of hydrogen at 50° C. for 18 hours after which the catalyst was removed by filtration and the filtrate concentrated in vacuo. Sodium carbonate (50% sat.) was added, and the precipitate, a pale brown solid, collected by filtration. Yield: 1.22 g, 90%; LCMS method: 2, RT: 2.13 min, MI: 390 [M+1]. 1H NMR (DMSO): 1.75-1.85 (m, 4H), 2.92-2.98 (m, 4H), 3.16 (t, 2H), 4.15 (t, 2H), 6.95 (d, 2H), 7.38 (d, 1H), 7.46 (d, 1H), 7.55 (d, 1H), 7.65 (d, 2H), 8.24 (s, 1H), 8.69 (s, 1H), 9.43 (s, 1H).

Workup

customwas removed by filtration
concentrationthe filtrate concentrated in vacuo
additionSodium carbonate (50% sat.) was added
filtrationthe precipitate, a pale brown solid, collected by filtration

Sources & evidence

ORD record: ord-50af21839ab64cdcba76ec4c0aba49ac
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431596B2

Reaction notes

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