2-Methoxyethylamine → 2-{6-[(2-Methoxyethyl)amino]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 37900

Reaction equation

HRID 37900 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][NH:9]2)[CH:3]=1.[CH3:20][O:21][CH2:22][CH2:23][NH2:24].C(N(CC)C(C)C)(C)C>C(O)CCC>[ClH:1].[CH3:20][O:21][CH2:22][CH2:23][NH:24][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][NH:9]2)[CH:3]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Product 1

HCID 708729362-{6-[(2-Methoxyethyl)amino]pyrimidin-4-yl}-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg (0.4 mmol) of the compound from Example 23, 64 μl (55 mg, 0.7 mmol) of 2-methoxyethylamine and 127 μl of N,N-diisopropylethylamine (94 mg, 0.7 mmol) are stirred in 3 ml of n-butanol under reflux for 1.5 h. The solvent is then removed completely on a rotary evaporator. The residue is stirred with diethyl ether/methanol, the precipitate is filtered off and the filter residue is washed with diethyl ether. The solid is stirred in 1.5 ml of 1 N hydrochloric acid and concentrated again, and the product is dried under reduced pressure.

Workup

  1. temperatureunder reflux for 1.5 h
  2. customThe solvent is then removed completely on a rotary evaporator
  3. filtrationthe precipitate is filtered off
  4. washthe filter residue is washed with diethyl ether
  5. stirringThe solid is stirred in 1.5 ml of 1 N hydrochloric acid
  6. concentrationconcentrated again
  7. customthe product is dried under reduced pressure

Sources & evidence

ORD record
ord-1791cde93cdc4f43a1bc5def2af81d03
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Linked notes

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