Trifluoroacetic acid → HCID 136411692, compound

HRID 1795962Notes

Reaction equation

HRID 1795962 reaction equation
FC(F)(F)C(O)=O.Cl.C(O[C:12]([C:14]1[N:15]([NH2:24])[CH:16]=[CH:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:13])C.[CH2:25]([N:27](CC)CC)[CH3:26]>CC#N>[CH2:22]([O:21][C:19]([C:18]1[CH:17]=[CH:16][N:15]2[C:14]=1[C:12](=[O:13])[NH:27][C:25]([CH3:26])=[N:24]2)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 71742792HCID 71742792, compound

Product 1

HCID 136411692HCID 136411692, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Trifluoroacetic acid (0.45 ml, 5.85 mmol) was added to a solution of 1-amino-1H-pyrrole-2,3-dicarboxylic acid diethyl ester, hydrochloride salt in CH3CN (20 ml) and heated to 85° C. for 12 h. The reaction mixture was concentrated in vacuo, diluted with CH3CN (20 ml), treated with triethylamine (1.36 ml, 11.9 mmol), and heated to 85° C. for 6 h. The reaction mixture was concentrated in vacuo, dissolved in EtOAc and the organic layer washed with 1 N HCl (1×50 ml), saturated NaHCO3 (3×50 ml), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a solid (0.20 g, 54%): 1H NMR (CDCl3) δ 7.27–7.32 (m, 1H), 7.01–7.02 (m, 1H), 4.32–4.38 (m, 2H), 2.41 (s, 3H), 1.90 (br m, 1H), 1.35–1.40 (m, 3H); MS (ESI+) 222 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with CH3CN (20 ml)
  3. temperatureheated to 85° C. for 6 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutiondissolved in EtOAc
  6. washthe organic layer washed with 1 N HCl (1×50 ml), saturated NaHCO3 (3×50 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f80cf434a754b29b4671d24936fce4c
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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