Methyl 4-amino-o-anisate → HCID 67394195, compound

HRID 1023741Notes

Reaction equation

HRID 1023741 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[S:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>>[CH3:15][O:16][C:17]1[CH:26]=[C:25]([NH:27][C:12]([C:6]2[S:7][C:8]([CH:9]([CH3:10])[CH3:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[O:14])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 2

HCID 168705Methyl 4-amino-o-anisateHCID 58420519HCID 58420519, compound

Product 1

HCID 67394195HCID 67394195, compoundYield 32.5%

Procedure

In the same manner as that of Example 24, 4,5-diisopropylthiophene-2-carboxylic acid (80 mg, 0.377 mmol) and methyl 2-methoxy-4-aminobenzoate (123 mg, 0.679 mmol) were condensed, the reaction mixture was treated in a conventional manner, and then the residue was purified by silica gel chromatography [n-hexane-ethyl acetate (40:1)] and recrystallized to obtain methyl 2-methoxy-4-[(4,5-diisopropylthiophene-2-carbonyl)amino]benzoate (46 mg, 32%) as colorless prisms.

Workup

  1. customcondensed
  2. additionthe reaction mixture was treated in a conventional manner
  3. customthe residue was purified by silica gel chromatography [n-hexane-ethyl acetate (40:1)]
  4. customrecrystallized

Sources & evidence

ORD record
ord-f703e50c7cb247089fde5f233e1e1366
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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