Triethylamine → N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methyl-2-thiophenecarboxamide

HRID 1419959

Reaktionsgleichung

Reaktionsgleichung von HRID 1419959
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].C(N(CC)CC)C.[NH2:17][C:18]1[CH:39]=[CH:38][C:21]([C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][N:27]3[CH:35]=[CH:36][CH:37]=[C:26]3[CH2:25]2)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl>[CH:37]1[CH:36]=[CH:35][N:27]2[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:24]([C:22]([C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:7]([C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[O:8])=[CH:39][CH:38]=3)=[O:23])[CH2:25][C:26]=12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27376053-Methyl-2-thenoyl ChlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 15340667N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methyl-2-thiophenecarboxamideAusbeute 113,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 318 mg of 3-methyl-2-thiophenecarbonyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of the 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 18 hours. The volatiles are concentrated in vacuo to give a residue which crystallizes from ethyl acetate to afford 800 mg of solid. The solid is dissolved in methylene chloride washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is filtered through hydrous magnesium silicate, dried with Na2SO4 and concentrated in vacuo to give a residue which crystallizes from ethyl acetate to afford 400 mg of the desired product as a white solid, m.p. 232°-235° C.

Aufarbeitung

  1. customThe bath is removed
  2. stirringthe reaction mixture stirred at room temperature for 18 hours
  3. concentrationThe volatiles are concentrated in vacuo
  4. customto give a residue which
  5. customcrystallizes from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-41371a27699640d49b054ae89d201188
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889001

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