Dimethylamine → N,N-dimethyl-2-[4-(2-methyl-4-m-tolylethynyl-imidazol-1-yl)-2-oxo-2H-pyridin-1-yl]-acetamide

HRID 2194449Notes

Reaction equation

HRID 2194449 reaction equation
[CH3:1][NH:2][CH3:3].C(O[C:7](=[O:31])[CH2:8][N:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[N:17]=[C:16]2[CH3:29])=[CH:11][C:10]1=[O:30])C>C(O)C>[CH3:1][N:2]([CH3:3])[C:7](=[O:31])[CH2:8][N:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[N:17]=[C:16]2[CH3:29])=[CH:11][C:10]1=[O:30]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 49872676[4-(2-Methyl-4-m-tolylethynyl-imidazol-1-yl)-2-oxo-2H-pyridin-1-yl]-acetic acid ethyl ester

Product 1

HCID 58111183N,N-dimethyl-2-[4-(2-methyl-4-m-tolylethynyl-imidazol-1-yl)-2-oxo-2H-pyridin-1-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2 ml of a 5.6M solution of dimethylamine in ethanol were added 70 mg (0.19 mmol) of [4-(2-methyl-4-m-tolylethynyl-imidazol-1-yl)-2-oxo-2H-pyridin-1-yl]-acetic acid ethyl ester (Example 13). The reaction vessel was closed and the yellow solution was stirred for 2 days at room temperature. The solution was then evaporated to dryness, the residue was triturated with a small amount of ethyl acetate and the product was filtered off, yielding 59 mg of the title compound as a white solid, MS: m/e=375.3 (M+H+).

Workup

  1. customThe reaction vessel was closed
  2. customThe solution was then evaporated to dryness
  3. customthe residue was triturated with a small amount of ethyl acetate
  4. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-7f0bdec34cea44b0bc2aaff7f2fee89f
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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