Dimethylformamide dimethyl acetal → HCID 58980884, Verbindung

HRID 1181339

Reaktionsgleichung

Reaktionsgleichung von HRID 1181339
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[CH3:18]OC(OC)N(C)C.[CH2:26]([O:28][CH:29]([O:41][CH2:42][CH3:43])[CH2:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[O:39][CH3:40])[CH3:27]>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:36]([C:35]4[CH:37]=[CH:38][C:32]([O:31][CH2:30][CH:29]([O:28][CH2:26][CH3:27])[O:41][CH2:42][CH3:43])=[C:33]([O:39][CH3:40])[CH:34]=4)[CH:18]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 114367644-(2,2-Diethoxyethoxy)-3-methoxyaniline

Produkt 1

HCID 58980884HCID 58980884, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (2.0 g, 7.47 mmol, Maybridge, Inc) in ethanol (20 mL) was added dimethylformamide dimethyl acetal (2.5 mL, 2.5 eq, Aldrich). The reaction mixture was refluxed in a 90° C. oil bath for 3 h at which point the solvents were removed by rotary evaporation. Coevaporation with toluene removed the excess dimethylformamide dimethyl acetal. To the resulting residue was added ethanol (20 mL) and 4-(2,2-diethoxyethoxy)-3-methoxyaniline (2.3 g, 1.2 eq, Example H1). The reaction mixture was heated to 100° C. for 36 hours. The solvent was removed by rotary evaporation and the product purified by column chromatography followed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%). 1H NMR (CDCl3) δ 1.22 (6H, t), 3.63-3.83 (4H, m), 3.90 (3H, s), 4.14 (2H, d, J=5.3 Hz), 4.92 (1H, t, J=5.2 Hz), 6.97 (2H), 7.06 (1H, d, J=8.5 Hz), 7.46 (2H, d, J=8.5 Hz), 7.58 (1H, s), 7.68 (2H, d, J=8.4 Hz), 8.24 (1H, br, s). LCMS m/z=501 (m+H+).

Aufarbeitung

  1. customwere removed by rotary evaporation
  2. customCoevaporation with toluene removed the excess dimethylformamide dimethyl acetal
  3. temperatureThe reaction mixture was heated to 100° C. for 36 hours
  4. customThe solvent was removed by rotary evaporation
  5. customthe product purified by column chromatography
  6. customfollowed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%)

Quellen und Nachweise

ORD-Eintrag
ord-5973a2071c764f3f86cac406276b2574
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285557B2

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