3,5-Dibromo-1-methylpyridin-2(1H)-one → (2R,5S)-tert-Butyl 4-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)-2,5-dimethylpiperazine-1-carboxylate

HRID 1021668Notes

Reaction equation

HRID 1021668 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](NC2N=CC(N3CCN(C(OC(C)(C)C)=O)CC3)=CC=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[NH2:30][C:31]1[N:36]=[CH:35][C:34]([N:37]2[C@@H:42]([CH3:43])[CH2:41][N:40]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:39]([CH3:51])[CH2:38]2)=[CH:33][CH:32]=1.BrC1C(=O)N(C)C=C(Br)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:30][C:31]2[N:36]=[CH:35][C:34]([N:37]3[C@@H:42]([CH3:43])[CH2:41][N:40]([C:44]([O:46][C:47]([CH3:49])([CH3:48])[CH3:50])=[O:45])[C@H:39]([CH3:51])[CH2:38]3)=[CH:33][CH:32]=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 86684213HCID 86684213, compound

Product 1

HCID 86684214(2R,5S)-tert-Butyl 4-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)-2,5-dimethylpiperazine-1-carboxylateYield 79%

Procedure

Following the procedures as described for compound 101i, reaction of 122b (766 mg, 2.50 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (668 mg, 2.50 mmol) afforded 122c as a yellow solid (978 mg, 79%). LCMS: [M+H]+ 492

Sources & evidence

ORD record
ord-9612228faeeb45edb3c7a7fd022e1a23
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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