Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:27])[NH:20][C:21]([CH3:26])=[CH:22][C:23]=2[CH2:24][CH3:25])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[Na].[CH3:29][S:30]([OH:32])=[O:31]>>[CH2:24]([C:23]1[CH:22]=[C:21]([CH3:26])[NH:20][C:19](=[O:27])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=[C:2]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:3]=1)=[O:15])[CH3:25]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared from 6-bromo-N-[(4-ethyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (70 mg, 0.162 mmol) and the sodium salt of methanesulfinic acid (33.5 mg, 0.325 mmol), in the same manner as described for example 91. The product was collected as a white solid (21 mg) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.17 (m, 3H), 1.47-1.56 (m, 6H), 2.15 (s, 3H), 2.58 (q, J=7.58 Hz, 2H), 3.03 (s, 3H), 4.33-4.47 (m, 2H), 5.17-5.30 (m, 1H), 5.94 (s, 1H), 8.01 (d, J=1.26 Hz, 1H), 8.45 (m, 1H), 8.53 (s, 1H), 8.78 (t, J=4.93 Hz, 1H); LCMS: (M+H)+=431.1
Workup
- customThe product was collected as a white solid (21 mg) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.17 (m, 3H), 1.47-1.56 (m, 6H), 2.15 (s, 3H), 2.58 (q, J=7.58 Hz, 2H), 3.03 (s, 3H), 4.33-4.47 (m, 2H), 5.17-5.30 (m, 1H), 5.94 (s, 1H), 8.01 (d, J=1.26 Hz, 1H), 8.45 (m, 1H), 8.53 (s, 1H), 8.78 (t, J=4.93 Hz, 1H)
Sources & evidence
- ORD record
- ord-c7c1603a48b54fefa3aaca67d5e36acb
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018382B2
Linked notes
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