4-amino-2,6-dimethylbenzoic acid → 4-[(Ethylamino)carbonylamino]-2,6-dimethyl benzoic acid

HRID 1936595Notes

Reaction equation

HRID 1936595 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:12])[CH:3]=1.C(Cl)CCl.C1C=CC2N([OH:26])N=NC=2C=1.[CH3:27][CH2:28][N:29]([CH:33](C)C)C(C)C>>[CH2:28]([NH:29][C:33]([NH:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:12])[CH:3]=1)=[O:26])[CH3:27]

Participants

3

Reactant 2

HCID 3136824-amino-2,6-dimethylbenzoic acidHCID 86583922HCID 86583922, compound

Product 1

HCID 206194214-[(Ethylamino)carbonylamino]-2,6-dimethyl benzoic acid

Procedure

The tri-hydrochloride salt of the product of Example 8, step 3 (2 g, 4.3 mmol) and 4-amino-2,6-dimethyl benzoic acid (710 mg, 4.3 mmol) (see preparation below) were subjected to the standard coupling conditions (EDC/HOBT/iPr2NEt). Purification via flash chromatography (2/1 hexanes/acetone, SiO2) gave 1.16 g (52%) of 8AA as a yellow foam.

Workup

  1. customPurification via flash chromatography (2/1 hexanes/acetone, SiO2)
  2. customgave 1.16 g (52%) of 8AA as a yellow foam

Sources & evidence

ORD record
ord-dfc4c7c4495d461c99c33c9d9a382a9e
Source dataset
uspto-grants-2002_05
Patent number
US06391865B1

Reaction notes

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