3-Methoxybenzoic Acid → HCID 178490485, compound

HRID 1760165Notes

Reaction equation

HRID 1760165 reaction equation
OC1C2N=NNC=2C=CC=1.C(N=C=NC(C)C)(C)C.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=O.[CH3:31][C:32]1[C:36]([NH2:37])=[C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[NH:34][N:33]=1>CN(C)C=O.O>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:37][C:36]1[C:32]([CH3:31])=[N:33][NH:34][C:35]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27]

Participants

7

Reactant 4

HCID 114613-Methoxybenzoic AcidHCID 12734DiisopropylcarbodiimideHCID 178418300HCID 178418300, compoundHCID 178434570HCID 178434570, compound

Product 1

HCID 178490485HCID 178490485, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

311 mg of hydroxybenzotriazole and 445 μl of diisopropylcarbodiimide were added to a solution of 160 mg of 3-methoxybenzoic acid in 10 ml of dimethylformamide, after which 200 mg of 3-methyl-5-phenyl-1H-pyrazol-4-ylamine were added; the mixture was then stirred at RT for 12 h, after which water was added and the whole was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 4 C17H15N3O2 (293.33); MS (ESI) 294 (M+H).

Workup

  1. extractionthe whole was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  5. customThe following was obtained

Sources & evidence

ORD record
ord-14bd8f15802a4b278802cd158e590c4f
Source dataset
uspto-grants-2005_01
Patent number
US06841556B2

Reaction notes

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