StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trifluoroacetic acid → 1-[5-Nitroindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

HRID 2293767
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2293767
CC(C)(O[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6])C.FC(F)(F)C(O)=O.[OH-].[Na+].[N+:35]([C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42](C(O)=O)=[CH:41]2)([O-:37])=[O:36].C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl.O.O1CCCC1>[N+:35]([C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]3[C:18]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:11][CH2:12]1)=[O:6])=[CH:41]2)([O-:37])=[O:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 3512915-Nitroindole-2-carboxylic acidHCID 214776271-[1,1-Dimethylethoxycarbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Produkt 1

HCID 21477599
1-[5-Nitroindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[1,1-dimethylethoxycarbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine (PREPARATION 66, 4.99 g) in methylene chloride (75 ml) under nitrogen at 0° is added trifluoroacetic acid (14.3 ml) over 1 min. The resulting mixture is warmed to 20°-25°, stirred for 15 hrs, and then added to a solution of sodium hydroxide (7.44 g) in water (175 ml) at 0°. The layers are separated, the aqueous phase is extracted with methylene chloride (3×70ml), and the combined organic layer is washed with saline (60 ml), dried over sodium sulfate, and concentrated under reduced pressure to give the unprotected intermediate (Rf =0.14, TLC, methanol/chloroform, 10/90). In a flame-dried flask under nitrogen, 5-nitroindole-2-carboxylic acid (2.13 g) and 1,1'-carbonyldiimidazole (1.75 g) are dissolved in dry tetrahydrofuran and stirred for 3 hrs at 20°-25°. Then a solution of the intermediate (2.57 g) in dry tetrahydrofuran (3ml) is added and the resulting mixture is stirred for 1.8 days. The reaction mixture is filtered to give the title compound, NMR (dimethylsulfoxide-de) 12.41, 8.65, 8.09, 7.58, 7.16, 7.11, 6.91, 4.57, 3.93, 3.00, 1.71, 1.31 and 0.84. The filtrate is concentrated and is triturated with cold methanol to give an additional mount of the title compound.

Aufarbeitung

  1. temperatureThe resulting mixture is warmed to 20°-25°
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with methylene chloride (3×70ml)
  4. washthe combined organic layer is washed with saline (60 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give the unprotected intermediate (Rf =0.14, TLC, methanol/chloroform, 10/90)
  8. stirringstirred for 3 hrs at 20°-25°
  9. stirringthe resulting mixture is stirred for 1.8 days
  10. filtrationThe reaction mixture is filtered

Quellen und Nachweise

ORD-Eintrag
ord-0f2f1753b7024f589544132e1dc728e1
Quelldatensatz
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05686610

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion