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

HRID 640148Notes

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-1d5e30d0951d42adaa690994c279350f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Reaction notes

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