반응 #92458

반응 방정식

1-ethylpiperazine

L-proline

N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide

potassium carbonate

→

crude residue

수율 18.0%

N-(5-(5-(4-ethylpiperazin-1-yl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide

수율 18.0%

용매

DMSO

반응 조건

후처리

1. 1
   기타The mixture was degassed by N2 bubbling for 10 min
2. 2
   기타Then seal tube
3. 3
   기타was closed
4. 4
   기타The mixture was quenched
5. 5
   추출extracted as in Example 1(d)
6. 6
   workup.DISTILLATIONThe solvent was distilled off

실험 절차

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]+

출처