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

HRID 534799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534799
[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]([CH3:39])[C:18]3[CH: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)=[CH:20][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]([CH3:39])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 592621161,1-Dimethylethyl (2S)-4-({4-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl) (methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Produkt 1

HCID 237290236-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamideAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl (2S)-4-({4-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D16) (0.518 g, 0.97 mmol) was dissolved in DCM (19.2 mL) and TFA (4.8 mL) added. The solution was stirred for 1.5 h then the solvent was removed in vacuo. The product was taken up in methanol and eluted through an SCX (10 g) column with 2M NH3 in methanol solution. The solvent was removed to give a colourless oil which was purified by column chromatography. Elution with a 0-5% (2M NH3 in methanol)/DCM gradient yielded the title compound as a colourless oil (0.379 g). δH (CDCl3, 400 MHz) 8.07 (1H, dd), 7.65 (1H, dd), 7.22 (2H, d), 7.04 (6H, m), 6.70 (1H, d), 3.48 (3H, s), 3.43 (2H, s), 3.13 (br.s), 2.95 (3H, m), 2.70 (2H, d), 2.04 (1H, m), 1.74 (1H, m), 1.05 (3H, d). MS (ES): MH+ 435.3.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. washeluted through an SCX (10 g) column with 2M NH3 in methanol solution
  3. customThe solvent was removed
  4. customto give a colourless oil which
  5. customwas purified by column chromatography
  6. washElution with a 0-5% (2M NH3 in methanol)/DCM gradient

Quellen und Nachweise

ORD-Eintrag
ord-7bf6236aa01a4b939eaec14d03330c4d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853218B2

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