HCID 44125257, compound → N-(6-(6-Chloro-5-(2-chloro-4-fluorophenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide
Reaction equation
ClC1N=CC(C2C=CC3N(C=C(NC(=O)C)N=3)N=2)=CC=1NS(C1C=CC(C(O)(C)C)=CC=1)(=O)=O.CC1(C)C(C)(C)OB([C:43]2[CH:44]=[CH:45][C:46]3[N:47]([CH:49]=[C:50]([NH:52][C:53](=[O:55])[CH3:54])[N:51]=3)[N:48]=2)O1.Br[C:58]1[CH:59]=[C:60]([NH:65][S:66]([C:69]2[CH:74]=[CH:73][C:72]([F:75])=[CH:71][C:70]=2[Cl:76])(=[O:68])=[O:67])[C:61]([Cl:64])=[N:62][CH:63]=1>>[Cl:64][C:61]1[N:62]=[CH:63][C:58]([C:43]2[CH:44]=[CH:45][C:46]3[N:47]([CH:49]=[C:50]([NH:52][C:53](=[O:55])[CH3:54])[N:51]=3)[N:48]=2)=[CH:59][C:60]=1[NH:65][S:66]([C:69]1[CH:74]=[CH:73][C:72]([F:75])=[CH:71][C:70]=1[Cl:76])(=[O:68])=[O:67]Participants
Procedure
Following the procedure described for compound N-(6-(6-chloro-5-(4-(2-hydroxypropan-2-yl)phenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 35), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (200 mg, 662 μmol) (Example 35, Step 3) was reacted with N-(5-bromo-2-chloropyridin-3-yl)-2-chloro-4-fluorobenzenesulfonamide (265 mg, 662 μmol) to afford the title compound as a grey solid (50 mg, 25% yield). MS (ESI positive ion) m/z: 495 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.12 (s, 3H), 7.33-7.43 (m, 1H), 7.77 (dd, J=8.61, 2.15 Hz, 1H), 7.83 (d, J=9.39 Hz, 1H), 7.99 (dd, J=8.80, 6.06 Hz, 1H), 7.99 (dd, J=8.80, 6.06 Hz, 1H), 8.12 (d, J=9.39 Hz, 1H), 8.33 (d, J=8.41 Hz, 2H), 8.91 (s, 1H), 10.82-10.92 (br s, 1H), 10.96 (s, 1H).
Sources & evidence
- ORD record
- ord-b3810c5876d14432b537462afd892dbf
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820665B2
Reaction notes
Loading…