N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide → 4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)-6-(6-(methylcarbamoyl)pyridin-3-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([CH3:16])[CH2:14][N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12]3)=[C:8]([C:21]([NH2:23])=[O:22])[CH:7]=[N:6][N:5]2[CH:24]=1.[CH3:25][NH:26][C:27](=[O:43])[C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1>>[CH3:16][C@H:15]1[CH2:14][N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][C@H:11]1[NH:10][C:9]1[C:4]2[N:5]([CH:24]=[C:2]([C:31]3[CH:30]=[N:29][C:28]([C:27](=[O:43])[NH:26][CH3:25])=[CH:33][CH:32]=3)[CH:3]=2)[N:6]=[CH:7][C:8]=1[C:21]([NH2:23])=[O:22]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared from 6-bromo-4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide using the method previously described in Step 2 of Example 191 and by replacing 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide. LCMS (method H) retention time=1.09 min. (MH+472.2). 1H NMR (500 MHz, DMSO-d6, appeared as rotomers) δ 11.19 (d, J=7.9 Hz, 1H), 9.11 (d, J=2.0 Hz, 1H), 8.70 (q, J=4.5 Hz, 1H), 8.51 (d, J=1.5 Hz, 1H), 8.41 (dd, J=8.2, 2.2 Hz, 1H), 8.31 (s, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.87 (br. s., 1H), 7.48 (d, J=1.5 Hz, 1H), 7.23 (br. s., 1H), 5.04-4.92 (m, 1H), 3.86-3.63 (m, 2H), 3.38 (d, J=1.5 Hz, 1H), 3.03 (t, J=9.9 Hz, 1H), 2.89 (s, 3H), 2.84 (d, J=5.0 Hz, 3H), 2.72-2.64 (m, 1H), 1.09 (d, J=6.9 Hz, 3H).
Sources & evidence
- ORD record
- ord-1b8d6bf3db2c40049863ce84edfffd64
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987268B2
Reaction notes
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