3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 1918942Notes

Reaction equation

HRID 1918942 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([NH2:10])[CH:5]=1.Br[C:12]1[C:13](=[O:20])[N:14]([CH3:19])[CH:15]=[C:16]([Br:18])[CH:17]=1>>[Br:18][C:16]1[CH:17]=[C:12]([NH:10][C:6]2[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:8]([CH3:9])[N:7]=2)[C:13](=[O:20])[N:14]([CH3:19])[CH:15]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 580437775-(Methoxymethyl)-1-methyl-1H-pyrazol-3-amine

Product 1

HCID 580441025-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneYield 71.4%

Procedure

Following Example 148a, 1.7 g of 176b and 3.2 g of 3,5-dibromo-1-methylpyridin-2(1H)-one were reacted to give 176c as a yellow solid (2.8 g, 70%). MS: [M+H]+ 327. 1H NMR (500 MHz, CDCl3) δ 7.86 (d, J=2.5, 1H), 7.38 (s, 1H), 6.88 (d, J=2.5, 1H), 5.86 (s, 1H), 4.41 (s, 2H), 3.82 (s, 3H), 3.58 (s, 3H), 3.36 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-77ed14701cff458495bda461dcad7e09
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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