Hydrochloric Acid → 3-(1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1891587Notes

Reaction equation

C([N:20]1[CH:24]=[C:23]([C:25]2[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.CO>O1CCCC1>[NH:20]1[CH:24]=[C:23]([C:25]2[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[N:21]1

Participants

Conditions

Temperature: 70 °C

Procedure

3-(1-Trityl-1H-pyrazol-4-yl)-pyridin-2-ylamine (2.3 g, 5.71 mmol) described in Manufacturing Example 32-1-3, 2 N hydrochloric acid (15 mL), methanol (15 mL) and tetrahydrofuran (10 mL) were stirred for 30 minutes at 70° C. The reaction solution was allowed to room temperature, and partitioned into water and ethyl acetate. Saturated sodium bicarbonate solution was added to the separated aqueous layer, which was then extracted with ethyl acetate 6 times. The ethyl acetate layers were combined and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=10:1) to obtain the title compound (625 mg, 68.3%).

Workup

customwas allowed to room temperature
custompartitioned into water and ethyl acetate
additionSaturated sodium bicarbonate solution was added to the separated aqueous layer, which
extractionwas then extracted with ethyl acetate 6 times
customthe solvent was evaporated under a reduced pressure
customThe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record: ord-d345d08e87ad42b8889198337d987952
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507530B2

Reaction notes

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