Sodium Hydroxide → {6-[4-(6,7-Dimethoxy-quinolin-4-yloxy)-phenyl]-pyridazin-3-yl}-phenyl-amine

HRID 1993362Notes

Reaction equation

[C:1]1([NH:7][C:8]2[N:13]=[N:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1.[OH-].[Na+]>CN(C=O)C.N1C=CC=CC=1.CCOC(C)=O>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][CH:23]=[C:22]2[O:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[N:12]=[N:13][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(6-phenylamino-pyridazin-3-yl)-phenol (Step 3, 0.25 g, 0.95 mmol), 4-chloro-6,7-dimethoxy-quinoline (0.212 g, 0.95 mmol), Cu powder 0.1 g) and NaOH pellet (0.1 g) in DMF/pyridine (1.5 mL/1.5 mL) was heated in a microwave (CEM Discover, 60 W, 120° C., ramp 12 min, hold 18 min). The reaction mixture was then diluted with 50 mL of EtOAc and washed with 20 mL of water followed by brine (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column (50% EtOAc/hexane to EtOAc) to afford the title compound as a white solid. MS (ESI pos. ion) m/z: 451.2(M+H). Calc'd Exact Mass for C27H23N4O3: 450.49.

Workup

washwashed with 20 mL of water
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by column (50% EtOAc/hexane to EtOAc)

Sources & evidence

ORD record: ord-6ba86fd802ba48b4b34a57fe4c0b57d2
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

Loading…