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 592643Notes

Reaction equation

HRID 592643 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.[C:30](OC(N1CCN(C2C=NC(N)=CC=2)[C@@H](C)C1)=O)(C)(C)C.BrC1C(=O)N(C)C=C(Br)C=1>>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:15]=[N:16][C:11]([NH:10][C:4]3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=3)=[CH:12][CH:13]=2)[C@@H:18]([CH3:30])[CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

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 procedures as described for compound 101i, reaction of 130b (4.0 g) and 3,5-dibromo-1-methylpyridin-2(1H)-one (5.5 g) afforded 130c as a yellow solid (5.4 g, 83%). LCMS: [M+H]+ 478

Sources & evidence

ORD record
ord-b790a0acd2bf410b9f330c9103f78d0e
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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