Potassium Carbonate → HCID 178504708, Verbindung

HRID 966466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966466
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[S:35]([CH3:38])(=[O:37])=[O:36])=[CH:25][C:24]=3[F:39])[C:18]2=[O:40])=[CH:12][C:9]=1[C:10]#[N:11].C[N:42](C=O)C.[OH2:46]>O>[F:7][C:8]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[S:35]([CH3:38])(=[O:37])=[O:36])=[CH:25][C:24]=3[F:39])[C:18]2=[O:40])=[CH:12][C:9]=1[C:10]([NH:42][OH:46])=[NH:11]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 691435262-Fluoro-5-[1-(3-fluoro-2'-methanesulfonyl-biphenyl-4-yl)-2-oxo-piperidin-3-ylamino]-benzonitrile

Produkt 1

HCID 178504708HCID 178504708, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of acetoxyhydroamic acid (27 mg, 2.5eq) and K2CO3 (98 mg, 5eq) in DMF/H2O (3:1, 4 ml) was stirred at room temperature for 20 min. To this mixture was added 2-fluoro-5-[1-(3-fluoro-2′-methanesulfonyl-biphenyl-4-yl)-2-oxo-piperidin-3-ylamino]-benzonitrile (68 mg, 0.141 mmol) prepared as described under Ex. 58a above. The whole was stirred and heated at 110° C. for 18 h. The mixture was diluted with water and extracted 3× with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated. Purification by reverse phase HPLC yielded the title compound (50 mg, 72%) 1H NMR (DMSO-d6) δ 8.11 (1H,d,J=8 Hz), 7.79 (1H,t,J=7, 3 Hz), 7.71 (1H,t,J=7, 73 Hz), 7.46 (2H,m), 7.37 (1H,d,J=11 Hz), 7.28 (1H,d,J=8 Hz), 7.18 (1H,t,J=9.5 Hz), 6.98 (1H,m), 6.85 (1H,m), 4.29 (1H,m), 3.72 (2H,t,J=6.2 Hz), 2.91 (3H,s), 2.28 (1H,m), 2.08 (2H,m), 1.84 (1H,m). MS 515.3 (M+H)+.

Aufarbeitung

  1. customprepared
  2. stirringThe whole was stirred
  3. temperatureheated at 110° C. for 18 h
  4. extractionextracted 3× with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-660857a2a1ed4ba09b41ee441c93c161
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951872B2

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