2-Ethylbutyric acid → {4-[4-(2-Ethyl-butyrylamino)-2-fluoro-phenyl]-piperazin-1-yl}-phenyl-acetic acid methyl ester

HRID 1927610

Reaktionsgleichung

Reaktionsgleichung von HRID 1927610
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4]([OH:6])=O)[CH3:2].N=C=N.C1C=CC2N(O)N=NC=2C=1.[CH3:22][O:23][C:24](=[O:46])[CH:25]([N:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][C:39]=2[F:45])[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-]>C(Cl)Cl>[CH3:22][O:23][C:24](=[O:46])[CH:25]([N:32]1[CH2:33][CH2:34][N:35]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][C:4](=[O:6])[CH:3]([CH2:1][CH3:2])[CH2:7][CH3:8])=[CH:40][C:39]=2[F:45])[CH2:36][CH2:37]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 5

HCID 69152-Ethylbutyric acidHCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 69304062[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester

Produkt 1

HCID 16667331{4-[4-(2-Ethyl-butyrylamino)-2-fluoro-phenyl]-piperazin-1-yl}-phenyl-acetic acid methyl esterAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 2-ethylbutyric acid (32 μL, 0.22 mmol), polymer-supported carbodiimide (240 mg, 0.29 mmol), and HOBt (33 mg, 0.25 mmol) in DCM (5 mL) was stirred at rt for 15 min. A solution of [4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester (50 mg, 0.15 mmol) in DCM (1 mL) was added and the mixture was stirred for 16 h. Polymer-bound tetraalkylammonium carbonate (PB-carbonate; 250 mg, 0.77 mmol) was added and the mixture was stirred for 2 h. The resins were removed by filtration and the filtrate was concentrated to give an oil, which was purified by PTLC to give a peach solid (37 mg, 57%). MS (ESI): mass calcd. for C25H32FN3O3, 441.54; m/z found, 442.5 [M+H]+. 1H NMR (CDCl3): 7.46-7.44 (m, 3H), 7.36-7.33 (m, 3H), 7.19-7.12 (m, 1H), 7.00 (br s, 1H), 6.87 (t, J=9.0, 1H), 4.06 (s, 1H), 3.70 (s, 3H), 3.09-3.08 (m, 4H), 2.64-2.62 (m, 4H), 2.02-1.95 (m, 1H), 1.70-1.67 (m, 2H), 1.56-1.53 (m, 2H), 0.94 (t, J=7.4, 6H).

Aufarbeitung

  1. stirringthe mixture was stirred for 16 h
  2. stirringthe mixture was stirred for 2 h
  3. customThe resins were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto give an oil, which
  6. customwas purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-60c4ddcbd4fd4ce590b4c39fd8a1f2f9
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

Verknüpfte Notizen

Wird geladen…