Potassium Hydroxide → HCID 57894279, compound

HRID 1822094Notes

Reaction equation

HRID 1822094 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-cffac39175cf4d079cd14761bff4026d
Source dataset
uspto-grants-2009_10
Patent number
US07608677B2

Reaction notes

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