Triethylamine → HCID 15896225, compound

HRID 1263394Notes

Reaction equation

HRID 1263394 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:13][C:14]1[CH:15]=[C:16]([C:20]2[C:24]([Br:25])=[CH:23][N:22]([CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>ClCCl.[Cl-].[Na+].O>[Br:25][C:24]1[C:20]([C:16]2[CH:15]=[C:14]([NH:13][C:10](=[O:11])[CH2:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:19]=[CH:18][CH:17]=2)=[N:21][N:22]([CH3:26])[CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27332463-Methoxyphenylacetyl chlorideHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 15896225HCID 15896225, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3-methoxyphenylacetyl chloride (0.02 ml, 0.12 mmol) in dichloromethane (0.75 ml) was added dropwise at 0° C. to a solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol) and triethylamine (0.02 ml, 0.13 mmol) in dichloromethane (0.75 ml). The resulting mixture was stirred at room temperature for 16 h and then poured into brine. The organic layer was washed with more brine then dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate-toluene, 1:1), giving the title compound (9 mg, 19%). Rf 0.30 (ethyl acetate-toluene, 1:1).

Workup

  1. washThe organic layer was washed with more brine
  2. dry with materialthen dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (ethyl acetate-toluene, 1:1)

Sources & evidence

ORD record
ord-1b75261940f74050a4f94afbfe33d6b0
Source dataset
uspto-grants-2003_04
Patent number
US06541209B1

Reaction notes

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