Potassium Iodide → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-piperidin-1-yl-pyrimidin-4-ylamino)-propionic acid

HRID 405022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405022
C([O:3][C:4](=[O:41])[CH:5]([NH:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36](Cl)[N:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[C:9]([F:32])[CH:8]=1)C.C(OC(=O)C(N)CC1C=CC(C2N=C([C:59]3[CH:64]=[CH:63][C:62]([NH:65][C:66](OC(C)(C)C)=O)=CC=3)ON=2)=C(F)C=1)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].ClC1N=C(Cl)C=CN=1>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[C:28]([O:27][C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:33][C:34]4[CH:39]=[CH:38][N:37]=[C:36]([N:65]5[CH2:62][CH2:63][CH2:64][CH2:59][CH2:66]5)[N:35]=4)[C:4]([OH:3])=[O:41])=[CH:8][C:9]=3[F:32])[N:17]=2)=[CH:19][CH:20]=1)=[O:26])([CH3:29])([CH3:31])[CH3:30]

Komponenten

8

Edukt 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 66630730Ethyl 2-amino-3-(4-(5-(4-((tert-butoxycarbonyl)amino)phenyl)-1,2,4-oxadiazol-3-yl)-3-fluorophenyl)propanoateHCID 866607833-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-chloro-pyrimidin-4-ylamino)-propionic acid ethyl ester

Produkt 1

HCID 666317953-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-piperidin-1-yl-pyrimidin-4-ylamino)-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-(2-chloro-pyrimidin-4-ylamino)-propionic acid ethyl ester. To solution of 2-Amino-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}propionic acid ethyl ester in DMF (20 mL) were added sodium carbonate (360 mg, 3.4 mmol), potassium iodide (10 mg), TBAB (10 mg), and 2,4-dichloro-pyrimidine (503 mg, 3.4 mmol). The mixture was heated at 50° C. for 4 hrs. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over sodium sulfate, filtrated, concentrated, and purified by chromatography to give the title compound (96 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b67db9a80ed34386a8f6c04ab3671bbc
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748412B2

Notizen zur Reaktion

Wird geladen…