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Sodium Carbonate → Racemic 4-(trans-2,5-dimethylpiperazine-1-yl)-1-phenylpyrido[3,4-d]pyridazine

HRID 1514382
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514382
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:17]1[N:22]=[N:21][C:20]([N:23]2[CH2:28][C@@H:27]([CH3:29])[NH:26][CH2:25][C@@H:24]2[CH3:30])=[C:19]2[CH:31]=[N:32][CH:33]=[CH:34][C:18]=12>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:30][C@H:24]1[CH2:25][NH:26][C@H:27]([CH3:29])[CH2:28][N:23]1[C:20]1[N:21]=[N:22][C:17]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:18]2[CH:34]=[CH:33][N:32]=[CH:31][C:19]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 876275031-Chloro-4-(rac-2,5-trans-dimethylpiperazine-1-yl)pyrido[3,4-d]pyridazine

Produkt 1

HCID 68796083Racemic 4-(trans-2,5-dimethylpiperazine-1-yl)-1-phenylpyrido[3,4-d]pyridazineAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (146 mg, 126 μmol), phenylboronic acid (461 mg, 3.78 mmol), 2 M sodium carbonate (2520 μl, 5.04 mmol), and 1-chloro-4-(trans-2,5-dimethylpiperazine-1-yl)pyrido[3,4-d]pyridazine 43 (700 mg, 2.52 mmol) were added to a round bottom flask. The reaction vessel was purged with nitrogen and toluene (25 mL) was added. The reaction was heated to 100° C. overnight. After cooling to RT, the reaction was diluted with 250 mL of ethyl acetate and washed with 1×50 mL of sat. NaHCO3 and 1×50 mL of brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (10:0.5:0.1 CH2Cl2:MeOH, Et3N) afforded racemic 4-(trans-2,5-dimethylpiperazine-1-yl)-1-phenylpyrido[3,4-d]pyridazine 44 (750 mg, 93% yield). 1H-NMR (400 MHz, CDCl3): δ 9.76 (d, J=1.2 Hz, 1H), 8.94 (d, J=5.5 Hz, 1H), 7.84 (dd, J=5.9, 1.2 Hz, 1H), 7.78 (m, 2H), 7.57 (m, 2H), 3.83 (dqd, J=10.2, 5.9, 3.1 Hz, 1H), 3.47 (dd, J=12.1, 2.7 Hz, 1H), 3.30 (dqd, J=9.8, 6.3, 2.7 Hz, 1H), 3.25 (dd, J=12.5, 3.1 Hz, 1H), 2.94 (dq J=12.1, 10.2 Hz, 1H), 2.73 (dd, J=12.1, 9.8 Hz, 1H), 1.17 (d, J=6.3 Hz, 1H), 1.11 (d, J=6.6 Hz, 1H). MS 319.2 (calc'd) 320.2 (M+H, found).

Aufarbeitung

  1. customThe reaction vessel was purged with nitrogen and toluene (25 mL)
  2. additionwas added
  3. temperatureAfter cooling to RT
  4. additionthe reaction was diluted with 250 mL of ethyl acetate
  5. washwashed with 1×50 mL of sat. NaHCO3 and 1×50 mL of brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (10:0.5:0.1 CH2Cl2:MeOH, Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-ece8357287fb46deafe8e9f8339aead6
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222251B2

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