Methylamine → HCID 178484694, compound
Reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=3[CH3:18])[C:11](=O)[C:10]2=[O:21])=[O:8])[N:4]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:3]=1.[CH3:29][NH2:30].[C:31](#[N:33])C>>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:17]2[C:12](/[C:11](=[N:33]\[CH3:31])/[C:10]([NH:30][CH3:29])=[O:21])=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=2[CH3:18])=[O:8])[N:4]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:3]=1Participants
Conditions
- Temperature
- -10 °C
Procedure
A suspension of 1-[[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]-5-chloro-7-methyl-1H-indole-2,3-dione (i.e. the crude product of Example 5) (4.80 g, 10 mmol) in acetonitrile (15 mL) was cooled to −10° C., and liquefied methylamine (0.35 g, 11 mmol) was added. The mixture was stirred for 1 hour at −10° C., then warmed to 0° C., and three more portions of liquefied methylamine (each 0.35 g, 11 mmol) were added periodically. Finally the reaction mass was filtered, and the solids were washed with acetonitrile (3×2 mL) and dried under nitrogen to afford the title product, a compound of the present invention, as off-white solids, 1.09 g. Almost immediately, more solids began to precipitate from the filtrate. These were filtered, washed with acetonitrile (3×2 mL), and dried under nitrogen to afford a second crop of the title product as light yellow crystals, 2.91 g, m.p. 230-234° C. (decomp.). The total isolated yield from both crops was 4.00 g (76.3%).
Workup
- temperaturewarmed to 0° C.
- filtrationFinally the reaction mass was filtered
- washthe solids were washed with acetonitrile (3×2 mL)
- customdried under nitrogen
Sources & evidence
- ORD record
- ord-b6844bf78ae2465abc8c31e1f0ec0473
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012499B2
Reaction notes
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