Potassium Carbonate → HCID 117777429, Verbindung

HRID 64180

Reaktionsgleichung

Reaktionsgleichung von HRID 64180
Br[C:2]1[CH:31]=[CH:30][C:5]2[N:6]([C:9]3[CH:10]=[C:11]([NH:23][S:24]([CH:27]4[CH2:29][CH2:28]4)(=[O:26])=[O:25])[CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=4[F:22])[CH:14]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[CH3:39].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[CH2:38]([N:40]1[CH2:45][CH2:44][N:43]([C:2]2[CH:31]=[CH:30][C:5]3[N:6]([C:9]4[CH:10]=[C:11]([NH:23][S:24]([CH:27]5[CH2:29][CH2:28]5)(=[O:26])=[O:25])[CH:12]=[C:13]([C:15]5[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=5[F:22])[CH:14]=4)[CH:7]=[N:8][C:4]=3[CH:3]=2)[CH2:42][CH2:41]1)[CH3:39]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 145742L-ProlineHCID 89501045N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

Produkt 1

HCID 117777429HCID 117777429, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of the compound of N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (110 mg, 0.198 mmol) in DMSO was added potassium carbonate (54 mg, 0.391 mmol, 2.0 eq.). The mixture was degassed by N2 bubbling for 10 min followed by addition of 1-ethylpiperazine (68 mg, 0.595 mmol, 3.0 eq.) and L-proline (4.5 mg) and CuI (3 mg). Then seal tube was closed and the mixture was kept at 95° C. for 24 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to give the product in 18% yield (20 mg). 1H NMR (400 MHz, DMSO-D6): δ10.3 (s, 1H), 8.98 (s, 1H), 7.77 (m, 1H), 7.66 (s, 1H), 7.60 (brs, 2H), 7.50 (brs, 2H), 7.41 (s, 1H), 7.33-7.27 (m, 2H), 3.60 (m, 4H), 3.29-3.20 (m, 4H), 3.02 (q, 2H), 2.90 (t, 1H), 1.30 (t, 3H), 1.04 (q, 4H), LC-MS (ESI): Calculated mass: 537.62; Observed mass: 538.1 [M+H]+

Aufarbeitung

  1. customThe mixture was degassed by N2 bubbling for 10 min
  2. customThen seal tube
  3. customwas closed
  4. customThe mixture was quenched
  5. extractionextracted as in Example 1(d)
  6. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-5c2d842e7c0f4712a8e85d08303f3378
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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