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 1411740Notes

Reaction equation

HRID 1411740 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.N[C:31]1N=CC(N2CCN(C(OC(C)(C)C)=O)C[C@@H]2C)=CC=1.BrC1C(=O)N(C)C=C(Br)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][C@@H:18]3[CH3:31])=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 58043929Tert-butyl 4-(6-((5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino)pyridin-3-yl)piperazine-1-carboxylateHCID 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 procedure described for compound 101i and starting with (3S)-tert-butyl-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 191f (4.0 g, 13.7 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5.5 g, 20.6 mmol) afforded 191g as a yellow solid (5.4 g, 83%). MS-ESI: [M+H]+ 478

Sources & evidence

ORD record
ord-b22461c6496d4688acde9434e84de6c3
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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