Trifluoroacetic acid → 6-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-methyl-5-{[(3S)-3-methyl-1-piperazinyl]methyl}-2-pyridinyl)-3-pyridinecarboxamide

HRID 644772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644772
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:40])[C:18]3[N:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[C:20]([CH3:39])[CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:40])[C:18]3[CH:19]=[C:20]([CH3:39])[C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:22][N:23]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 592621991,1-Dimethylethyl (2S)-4-({6-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]-4-methyl-3-pyridinyl}methyl)-2-methyl-1-piperazinecarboxylate

Produkt 1

HCID 237289156-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-methyl-5-{[(3S)-3-methyl-1-piperazinyl]methyl}-2-pyridinyl)-3-pyridinecarboxamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl (2S)-4-({6-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]-4-methyl-3-pyridinyl}methyl)-2-methyl-1-piperazinecarboxylate (D118) (26 mg, 0.047 mmol) was dissolved in dry DCM (4 mL). TFA (1 mL) was added and the reaction mixture was stirred at room temperature, under argon. The reaction mixture was concentrated, re-dissolved in methanol (2 mL) and loaded on to a 1 g SCX cartridge. Elution with methanol (20 mL) followed by 2M NH3 in methanol (20 mL) gave a colourless oil. The product was further purified by MDAP. The resulting oil was dissolved in methanol (1 mL) and loaded on to a 1 g SCX cartridge and eluted with methanol (20 mL), followed by 2M NH3 in methanol (20 mL) to give the title compound as a colourless oil (15 mg). MS (ES): MH+ 450.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionre-dissolved in methanol (2 mL)
  3. washElution with methanol (20 mL)
  4. customgave a colourless oil
  5. customThe product was further purified by MDAP
  6. dissolutionThe resulting oil was dissolved in methanol (1 mL)
  7. washeluted with methanol (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-958e04bf831f458984bb86a05478ebc7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700599B2

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