2-Methoxyphenylacetic acid → HCID 22594961, compound

HRID 1872287Notes

Reaction equation

HRID 1872287 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([Br:13])=[CH:11][N:10]([CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24](O)=[O:25].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[Br:13][C:12]1[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:24](=[O:25])[CH2:23][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][CH3:15])[CH:7]=[CH:6][CH:5]=2)=[N:9][N:10]([CH3:14])[CH:11]=1

Participants

8

Reactant 5

HCID 71342-Methoxyphenylacetic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)AnilineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22594961HCID 22594961, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol), 2-methoxyphenylacetic acid (20 mg, 0.12 mmol), 1-hydroxybenzotriazole hydrate (16 mg, 0.12 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (46 mg, 0.12 mmol) were dissolved in chloroform (1.5 ml). N,N-Diisopropylethylamine (0.02 ml, 0.13 mmol) was added and the mixture stirred at room temperature for 16 h. The reaction mixture was then poured into brine and the organic layer washed with further brine, dried over magnesium sulphate and then concentrated in vacuo. The crude product was purified by column chromatography (chloroform-methanol, 99:1), giving the title compound (18 mg, 38%) as a colourless solid. Rf 0.65 (chloroform-methanol, 98:2).

Workup

  1. washthe organic layer washed with further brine
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (chloroform-methanol, 99:1)

Sources & evidence

ORD record
ord-829b00e0d71f4c509caff1d3c52453ef
Source dataset
uspto-grants-2000_08
Patent number
US06107324

Reaction notes

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