(R)-N-(piperidin-3-yl)-2-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-4-amine → HCID 178420604, compound

HRID 1500782Notes

Reaction equation

HRID 1500782 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[N:16][N:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=34)[N:9]=2)[CH2:2]1.Br[C:24]1[N:28]=[CH:27][NH:26][N:25]=1>>[N:25]1[N:26]=[C:27]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8]3[CH:13]=[CH:12][N:11]=[C:10]([C:14]4[CH:15]=[N:16][N:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=45)[N:9]=3)[CH2:2]2)[NH:28][CH:24]=1

Participants

3

Reactant 2

HCID 86691791(R)-N-(piperidin-3-yl)-2-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-4-amineHCID 178419478HCID 178419478, compound

Product 1

HCID 178420604HCID 178420604, compoundYield 52.1%

Conditions

Temperature
150 °C

Procedure

A mixture of (R)—N-(piperidin-3-yl)-2-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-4-amine (Preparation 34, 298 mg, 1.01 mmol) and 3-bromo-1H-1,2,4-triazole (75 mg, 0.51 mmol, prepared as described in Journal of Medicinal Chemistry, 2004, 47 (19), 4645-4648) was heated at 150° C. overnight. The crude mixture was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (96 mg, 52%) as a white solid.

Workup

  1. customThe crude mixture was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid

Sources & evidence

ORD record
ord-0eafb4628c0a42f995539f3130aefa85
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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