5-Bromo-1-methyl-3-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one → 5-Bromo-3-(5-((2S,5R)-2,5-dimethyl-4-(oxetan-3-yl)piperazin-1-yl)-pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

HRID 1021669Notes

Reaction equation

HRID 1021669 reaction equation
BrC1C=C(NC2C=CC(N3CCN([CH:23]4[CH2:26][O:25][CH2:24]4)CC3)=CN=2)C(=O)N(C)C=1.[Br:27][C:28]1[CH:29]=[C:30]([NH:36][C:37]2[N:42]=[CH:41][C:40]([N:43]3[C@@H:48]([CH3:49])[CH2:47][N:46](C(OC(C)(C)C)=O)[C@H:45]([CH3:57])[CH2:44]3)=[CH:39][CH:38]=2)[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1>>[Br:27][C:28]1[CH:29]=[C:30]([NH:36][C:37]2[CH:38]=[CH:39][C:40]([N:43]3[CH2:44][C@@H:45]([CH3:57])[N:46]([CH:23]4[CH2:26][O:25][CH2:24]4)[CH2:47][C@@H:48]3[CH3:49])=[CH:41][N:42]=2)[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1

Participants

3

Reactant 2

HCID 580437945-Bromo-1-methyl-3-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-oneHCID 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-carboxylate

Product 1

HCID 866837065-Bromo-3-(5-((2S,5R)-2,5-dimethyl-4-(oxetan-3-yl)piperazin-1-yl)-pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneYield 91%

Procedure

Following the procedures as described for compound 101k, reaction of 122d (700 mg, 1.79 mmol), afforded 122e as a yellow solid (723 mg, 91%). LCMS: [M+H]+ 448

Sources & evidence

ORD record
ord-134300703edd4b13a53668b8f170214e
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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