Trifluoroacetic acid → HCID 18353832, compound

HRID 430031Notes

Reaction equation

HRID 430031 reaction equation
[O:1]=[C:2]([NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].FC(F)(F)C(O)=O>O1CCCC1>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2](=[O:1])[NH:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7243O-PhenylenediamineHCID 18353833HCID 18353833, compound

Product 1

HCID 18353832HCID 18353832, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

0.34 g (2.1 mmole) of N,N′-carbonyldiimidazole was added to a tetrahydrofuran (10 ml) suspension including 0.6 g (2.1 mmole) of 4-{2-oxo-2-[(pyridin-3-ylmethyl)amino]ethoxy}benzoic acid, followed by stirring at 45° C. for 1 hour. After cooling to room temperature, 2.1 g (19.4 mmole, 8 equivalents) of 1,2-phenylenediamine and 0.4 ml of trifluoroacetic acid were added, and reaction was further carried out for 15 hours. After completion of the reaction, a post-treatment was performed in the same manner as in Example 6 to obtain 0.67 g (yield: 53%) of N-(2-aminophenyl)-4-{2-oxo-2-[(pyridin-3-ylmethyl)amino]ethoxy}-benzamide.

Workup

  1. temperatureAfter cooling to room temperature
  2. customreaction
  3. waitwas further carried out for 15 hours
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-8b714be84fd941afa45d76e5713ea271
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

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