Triethylamine → HCID 67220707, compound

HRID 1865025Notes

Reaction equation

HRID 1865025 reaction equation
C(N(CC)CC)C.Cl.Cl[C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.[CH:19]1([CH2:22][NH:23][C:24]2[C:25]([S:43][CH3:44])=[N:26][N:27]3[C:32]([C:33]4[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=4[O:41][CH3:42])=[CH:31][CH:30]=[CH:29][C:28]=23)[CH2:21][CH2:20]1.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[CH:19]1([CH2:22][N:23]([C:24]2[C:25]([S:43][CH3:44])=[N:26][N:27]3[C:32]([C:33]4[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=4[O:41][CH3:42])=[CH:31][CH:30]=[CH:29][C:28]=23)[C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[N:18][CH:10]=2)[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27628002-Chloropyridine-3-carboxylic acid--hydrogen chloride (1/1)HCID 21984576N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Product 1

HCID 67220707HCID 67220707, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.038 mL) and chloronicotinic acid hydrochloride (20 mg) were added to a solution of N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (33 mg) in dichloromethane (0.8 mL) while cooling on ice, and the mixture was stirred at the same temperature for 1 hour. Saturated aqueous sodium hydrogencarbonate was added while cooling on ice, extraction was performed with ethyl acetate, and the extract washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:2) to obtain the title compound (36 mg) as white crystals.

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice, extraction
  3. washthe extract washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:2)

Sources & evidence

ORD record
ord-2d86c59e6ba446a6a355f3cb5387bb55
Source dataset
uspto-grants-2009_12
Patent number
US07625925B2

Reaction notes

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