3,5-Dibromo-1-methylpyridin-2(1H)-one → (S)-3-[[5-(4-Boc-2-methyl-1-piperazinyl)-2-pyridyl]amino]-5-bromo-1-methylpyridin-2(1H)-one

HRID 1412137Notes

Reaction equation

HRID 1412137 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]2[CH3:21])=[CH:4][CH:3]=1.Br[C:23]1[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[C:27]([Br:29])[CH:28]=1>>[Br:29][C:27]1[CH:28]=[C:23]([NH:1][C:2]2[N:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]3[CH3:21])=[CH:4][CH:3]=2)[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 86683730(3S)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 86683729(S)-3-[[5-(4-Boc-2-methyl-1-piperazinyl)-2-pyridyl]amino]-5-bromo-1-methylpyridin-2(1H)-oneYield 83%

Procedure

Following the procedures of Example 323c, and starting with 340b (4.0 g, 13.7 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5.5 g, 20.6 mmol) afforded 340c as a yellow solid (5.4 g, 83%). MS-ESI: [M+H]+ 478

Sources & evidence

ORD record
ord-04c0e46db3eb4a5492eeb5085c5397ac
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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