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

HRID 1690972Notes

Reaction equation

HRID 1690972 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 592552153-(1-Trityl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 592552903-(1H-pyrazol-4-yl)-pyridin-2-ylamineYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-0e7a4933ecc64220a3639c838a0d8f66
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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