Thiophene-3-carboxylic acid → HCID 15434276, Verbindung

HRID 841914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841914
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:19]=1>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[O:8])[CH2:28][CH2:29]2)[N:19]=1

Komponenten

5

Edukt 3

HCID 6918Thiophene-3-carboxylic acidHCID 8471TriethylamineHCID 114809874-Methoxy-2-(piperazin-1-yl)pyrimidine

Produkt 1

HCID 15434276HCID 15434276, VerbindungAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1.0 g (7.81 mmol) of 3-thienylcarboxylic acid and 1 mL (7.86 mmol) of triethylamine in 30 mL of CH2Cl2 cooled to 0° C. 0.84 g (7.81 mmol) of ethyl chloroformiate are added. The mixture is maintained at 0° C. for 20 minutes and then 1.5 g (7.81 mmol) of 4-methoxy-2-(1-piperazinyl) pyrimidine dissolved in 10 mL of CH2Cl2 are added to the solution. The temperature is allowed to rise to room temperature and the solution continually stirred for 2 hours and the organic phase is washed with H2O, dried over NaSO4 and the solvent evaporated off under reduced pressure. The resulting oil is treated with ethyl ether to yield a solid which is recrystallised from ethanol/H2O to give 0.8 g (2.63 mmol) of 4-methoxy-2-[4-(3-thienylcarbonyl)-1-piperazinyl]pyrimidine. m.p.=90-92° C.

Aufarbeitung

  1. addition0.84 g (7.81 mmol) of ethyl chloroformiate are added
  2. additionare added to the solution
  3. customto rise to room temperature
  4. washthe organic phase is washed with H2O
  5. dry with materialdried over NaSO4
  6. customthe solvent evaporated off under reduced pressure
  7. additionThe resulting oil is treated with ethyl ether
  8. customto yield a solid which
  9. customis recrystallised from ethanol/H2O

Quellen und Nachweise

ORD-Eintrag
ord-79c7ccc44e42476d8b7a47ac5e839548
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372746B1

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