Water → N-(1-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}piperidin-4-yl)-2-(4-methylphenyl)acetamide

HRID 39581

Reaktionsgleichung

Reaktionsgleichung von HRID 39581
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[NH:40][C:41]2[CH:46]=[CH:45][C:44]([I:47])=[CH:43][C:42]=2[F:48])=[O:33])[CH2:28][CH2:27]1.O>CS(C)=O>[F:48][C:42]1[CH:43]=[C:44]([I:47])[CH:45]=[CH:46][C:41]=1[NH:40][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][C:34]=1[C:32]([N:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:8](=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][C:1]([CH3:11])=[CH:6][CH:5]=2)[CH2:27][CH2:28]1)=[O:33]

Komponenten

6

Edukt 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 248474p-Tolylacetic acidHCID 672519504-[(4-aminopiperidin-1-yl)carbonyl]-N-(2-fluoro-4-iodophenyl)pyridin-3-amine hydrochloride

Produkt 1

HCID 11548696N-(1-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}piperidin-4-yl)-2-(4-methylphenyl)acetamideAusbeute 109,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of p-tolyl acetic acid (0.027 g, 0.180 mmol) and CDI (0.036 g, 0.222 mmol) in dry DMSO (2 mL) was heated to 50° C. for 2 h prior to addition of 4-[(4-aminopiperidin-1-yl)carbonyl]-N-(2-fluoro-4-iodophenyl)pyridin-3-amine hydrochloride (described above) (0.052 g, 0.109 mmol). The contents were then stirred at room temp. After 6 h, HPLC indicated near-complete reaction. The contents were poured into water (30 mL) and extracted with ethyl acetate (30 mL). The organics were washed with brine (2×30 mL), dried over sodium sulfate and concentrated to a yellow oil. The oil was further dried under high vacuum for 2 h at 40° C. to provide the desired product as a yellow semi-solid (0.068 g, 0.119 mmol, 66%). LC/MS [8.92 min; 573 (M+1)]

Aufarbeitung

  1. customreaction
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organics were washed with brine (2×30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a yellow oil
  6. customThe oil was further dried under high vacuum for 2 h at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-65078b1124f04b66851cf06ce5825cb7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524911B2

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