Sodium → 6-(cyclopropylsulfonyl)-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

HRID 1476473

Reaction equation

HRID 1476473 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].[CH:29]1([S:32]([OH:34])=[O:33])[CH2:31][CH2:30]1>>[CH:29]1([S:32]([C:2]2[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:27])[NH:20][C:21]([CH3:26])=[CH:22][C:23]=3[CH2:24][CH3:25])=[O:15])[C:5]3[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=3[CH:10]=2)(=[O:34])=[O:33])[CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 5360545SodiumHCID 14563239Cyclopropanesulfinic acidHCID 545964916-bromo-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

Product 1

HCID 545964966-(cyclopropylsulfonyl)-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

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 cyclopropanesulfinic acid (41.9 mg, 0.325 mmol) in the same manner as described for example 91. The product was collected an off-white solid (52 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.16 (m, 5H), 1.19-1.27 (m, 2H), 1.50 (d, J=6.57 Hz, 6H), 2.15 (s, 3H), 2.58 (m, 2H), 2.97 (m, 1H), 4.41 (d, J=4.80 Hz, 2H), 5.26 (m, 1H), 5.94 (s, 1H), 8.01 (d, J=1.26 Hz, 1H), 8.43 (s, 1H), 8.53 (s, 1H), 8.83 (m, 1H), 11.58 (s, 1H); LCMS: (M+H)+=457.0

Workup

  1. customThe product was collected an off-white solid (52 mg)

Sources & evidence

ORD record
ord-902798d88c6f4034adb85c10c4c4336b
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Linked notes

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