3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-1-methyl-3-(1-methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

HRID 593102Notes

Reaction equation

HRID 593102 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][N:8]([CH3:13])[CH:9]2[CH2:12][O:11][CH2:10]2)=[CH:5][C:4]([NH2:14])=[N:3]1.Br[C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=1>>[Br:22][C:20]1[CH:21]=[C:16]([NH:14][C:4]2[CH:5]=[C:6]([CH2:7][N:8]([CH3:13])[CH:9]3[CH2:10][O:11][CH2:12]3)[N:2]([CH3:1])[N:3]=2)[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 580437871-Methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-amine

Product 1

HCID 580437865-Bromo-1-methyl-3-(1-methyl-5-((methyl(oxetan-3-yl)amino)methyl)-1H-pyrazol-3-ylamino)pyridin-2(1H)-oneYield 63%

Procedure

Following the procedure in Example 292c, and starting with 302c and 3,5-dibromo-1-methylpyridin-2(1H)-one afforded 302d in 63% yield. LCMS: (M+H)+ 383. 1H NMR (500 MHz, DMSO) δ 8.35 (s, 1H), 7.99 (d, J=2.5, 1H), 7.36 (d, J=2.5, 1H), 5.99 (s, 1H), 4.50 (t, J=7, 2H), 4.40 (t, J=6.5, 2H), 3.77 (s, 3H), 3.57 (m, 1H), 3.49 (s, 3H), 3.35 (s, 2H), 2.01 (s, 3H).

Sources & evidence

ORD record
ord-2327c4c316b6434bb7e034ccaefa5c60
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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