Triethylamine → 5-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide

HRID 381499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381499
[C:1]1([C:7]2[NH:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN[O:18][CH3:19].Cl.C(N=C=NCCC[N:29]([CH3:31])C)C.O.OC1C2N=NNC=2C=CC=1.CCN(CC)CC>>[CH3:19][O:18][CH2:31][NH:29][C:12]([C:10]1[NH:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=1)=[O:14]

Komponenten

6

Edukt 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2261995-phenyl-1H-pyrrole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 544094405-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide

Versuchsvorschrift

To a 200 mL round bottomed flask with a stirring bar and an argon inlet was added 5-phenyl-1H-pyrrole-2-carboxylic acid AV-5-1 (2.45 g, 13.09 mmol), N,O-dimethylhydroxylamine hydrochloride (1.40 g, 14.40 mmol), N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride (2.76 g, 14.40 mmol), hydroxybenztriazole hydrate (1.94 g, 14.40 mmol) and dry, degassed DMF (25 mL). This well stirred mixture was warmed gently until all of the solids dissolved. Et3N (5.6 mL, 40.00 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature 18 h. The solvents were removed in vacuo at +80° C. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The layers were separated and the organic phase was washed with H2O (2×) and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave a solid. This material was chromatographed on silica gel using 35% EtOAc in hexane as eluant to give 5-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide AV-6-1 as a solid. 1H NMR (CDCl3) δ 3.36 (3H, s), 3.80 (3H, s), 6.58 (1H, dd, j=2.2, 4.0 Hz), 6.94 (1H, dd, j=2.2, 4.0 Hz), 7.30 (1H, m), 7.41 (2H, m), 7.58 (2H, m), 9.63 (1H, br s).

Aufarbeitung

  1. customdry
  2. customdegassed DMF (25 mL)
  3. temperaturewas warmed gently until all of the solids
  4. dissolutiondissolved
  5. stirringThe resulting mixture was stirred at ambient temperature 18 h
  6. customThe solvents were removed in vacuo at +80° C
  7. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  8. customThe layers were separated
  9. washthe organic phase was washed with H2O (2×) and brine
  10. customDrying
  11. filtration(MgSO4), filtration and removal of the solvent in vacuo
  12. customgave a solid
  13. customThis material was chromatographed on silica gel using 35% EtOAc in hexane as eluant

Quellen und Nachweise

ORD-Eintrag
ord-c1f6ac9b5c0743048bb2b31d4f7905a8
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306891B1

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