Cyclopropylamine → Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylate

HRID 1874970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874970
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]

Komponenten

4

Edukt 2

HCID 69828CyclopropylamineHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 68484245Methyl 3-chloro-5-[(cyclopropylamino)carbonyl]-1H-pyrrole-2-carboxylateAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cycloproplyamine (0.166 g, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. The solvent was evaporated and purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexanes) to afford the title compound (0.099 g, 70%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.81 (br. s., 1H), 7.71 (br. s., 1H), 6.78 (s, 1H), 3.84 (s, 3H), 2.79-2.92 (m, 1H), 0.73 (d, 2H), 0.57 (d, 2 H) LCMS: m/z 243.1 (M+1).

Aufarbeitung

  1. customThe solvent was evaporated
  2. custompurification

Quellen und Nachweise

ORD-Eintrag
ord-ea2b2e9b11064fb083e91dc628a5f7d5
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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