N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide → N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(4-fluoro-3-(morpholine-4-carbonyl)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14](C4C=CC=C(F)C=4)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30].ClC1N=CC(C2C=CC3N(C(I)=C(NC(=O)C)N=3)N=2)=CC=1NS(C)(=O)=O.[F:59][C:60]1[CH:65]=[CH:64][C:63](B(O)O)=[CH:62][C:61]=1[C:69]([N:71]1[CH2:76][CH2:75][O:74][CH2:73][CH2:72]1)=[O:70]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:63]4[CH:64]=[CH:65][C:60]([F:59])=[C:61]([C:69]([N:71]5[CH2:76][CH2:75][O:74][CH2:73][CH2:72]5)=[O:70])[CH:62]=4)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:28][S:29]([CH3:32])(=[O:30])=[O:31]Participants
Reactant 3
Product 1
Procedure
Following the procedure described for N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 22), N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (0.0650 g, 0.128 mmol) (Example 21) was reacted with 4-fluoro-3-(morpholine-4-carbonyl)phenylboronic acid (0.0390 g, 0.154 mmol, Combi-Blocks, San Diego, Calif.) at 90° C. for 3 h to afford the title compound as a yellow solid (0.058 g, 64%). MS (ESI, positive ion) m/z: 588 (M−TFA+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 3H), 3.20 (s, 3H), 3.32 (s, 2H), 3.51-3.58 (m, 2H), 3.67 (br s, 4H), 7.45 (t, J=9.1 Hz, 1H), 7.80 (d, J=4.9 Hz, 1H), 7.99 (d, J=9.6 Hz, 1H), 8.04-8.09 (m, 1H), 8.31 (d, J=9.4 Hz, 1H), 8.48 (d, J=2.3 Hz, 1H), 8.93 (d, J=2.2 Hz, 1H), 9.93 (s, 1H), 10.28 (br s, 1H).
Sources & evidence
- ORD record
- ord-268c1a6bd01f4449b72e0b9eca4b8980
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820665B2
Reaction notes
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