N-(2-Aminophenyl)-4-methoxybenzamide → HCID 86628412, compound

HRID 1445454Notes

Reaction equation

HRID 1445454 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:25])([CH3:24])[CH2:11][O:12][C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][O:27][C:28]1[CH:43]=[CH:42][C:31]([C:32]([NH:34][C:35]2[C:36]([NH2:41])=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:33])=[CH:30][CH:29]=1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:25])([CH3:24])[CH2:11][O:12][C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15]([NH:41][C:36]1[C:35]([NH:34][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[CH:43][CH:42]=2)=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 68545087HCID 68545087, compound

Product 1

HCID 86628412HCID 86628412, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner substantially equivalent to Example 101-D, 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-methoxybenzoic acid (2.92 g, 8.25 mmol) and N1-(4-methoxybenzoyl)-1,2-benzenediamine (2.00 g, 8.25 mmol) were coupled. The crude material was dissolved in dichloromethane, and aminomethylated polystyrene was added to remove the unreacted acid chloride. The resin was filtered, the solution added directly to a SCX column (Varian, 60 cc/10 g, prewashed with MeOH), and the product washed through the column with 9:1 CHCl3:MeOH. Concentration of the wash in vacuo gave 3.50 g (73.4%) of a white foam.

Workup

  1. customto remove the unreacted acid chloride
  2. filtrationThe resin was filtered
  3. additionthe solution added directly to a SCX column (Varian, 60 cc/10 g, prewashed with MeOH)
  4. washthe product washed through the column with 9:1 CHCl3
  5. washConcentration of the wash in vacuo

Sources & evidence

ORD record
ord-2a21415cd9ae4378b755360523a0801a
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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