Potassium Hydroxide → HCID 57894279, compound

HRID 638777Notes

Reaction equation

HRID 638777 reaction equation
C1(C)C(S([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15](=[O:36])[C:16]2[CH:21]=[C:20]([NH:22]C(=O)C(F)(F)F)[CH:19]=[C:18]([NH:29]C(=O)C(F)(F)F)[CH:17]=2)(=O)=O)=CC=CC=1.[OH-].[K+]>CCO>[NH2:29][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([NH2:22])[CH:19]=1)[C:15]([C:11]1[NH:10][CH:14]=[CH:13][CH:12]=1)=[O:36]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86618066HCID 86618066, compound

Product 1

HCID 57894279HCID 57894279, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred EtOH (10 mL) solution of N-toluenesulfonyl-2-(3,5-di(trifluoroacetylamino)benzoyl)pyrrole (1.00 g, 1.83 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until TLC analysis showed complete conversion. The resulting solution was cooled to room temperature and worked up as in Example 7. The crude product was purified by column chromatography (SiO2, CH2Cl2:MeOH) to afford the purified product 2-(3,5-diaminobenzoyl)pyrrole (237 mg, 65% yield). 1H NMR (500 MHz, CD3OD, 25° C.) δ 2.43 (s, 3H), 6.45 (m, 1H), 6.90 (m, 1H), 7.41 (d, 2H), 7.88 (m, 3H), 7.93 (d, 2H), 8.39 (t, 1H); 13C NMR (100 MHz, CD3OD, 25° C.) δ 104.8, 105.7, 109.4, 119.5, 125.2, 130.5, 139.8, 147.8, 186.0; HRMS (EI): m/z 201.0896 (100) {M}+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux until TLC analysis
  3. customThe crude product was purified by column chromatography (SiO2, CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-a697ab2f99294849abf60f93f1a87cc6
Source dataset
uspto-grants-2010_04
Patent number
US07691494B2

Reaction notes

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