Dimethylformamide → methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycine

HRID 843640Notes

Reaction equation

HRID 843640 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[N:7]=[C:6]([NH:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[N:5]=1.C[O:29][C:30](=[O:33])[CH2:31]Cl.[CH3:34]N(C=O)C>>[CH3:34][CH:31]([C:30]([OH:29])=[O:33])[N:19]([C:20]1[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=1)[C:6]1[N:5]=[C:4]([NH2:3])[N:9]=[C:8]([CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[N:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7295Methyl chloroacetateHCID 24758Sodium hydrideHCID 4863624-[[4-Amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 22281687methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycineYield 19.4%

Conditions

Temperature
70 °C

Procedure

A solution of sodium hydride (0.00195 mol) in DMF (7 ml) was added to compound (1) (0.00186 mol) and the resulting solution was stirred for 5 minutes under argon. Then, chloroacetic acid methyl ester (0.0186 mol) was added and the reaction mixture was heated to 70° C. for 19 hours. The reaction mixture was then quenched with water and the resulting solid was filtered off. The residue was treated with hot ACN, then filtered while still hot. The residue from the cooled filtrate was recrystallized from 1,4-dioxane. The precipitate was filtered off, yielding 0.16 g (19.4%) of methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycine (compound 39).

Workup

  1. customThe reaction mixture was then quenched with water
  2. filtrationthe resulting solid was filtered off
  3. additionThe residue was treated with hot ACN
  4. filtrationfiltered while still hot
  5. customThe residue from the cooled filtrate was recrystallized from 1,4-dioxane
  6. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-d3912ec6ba804d89a13321bdc516d902
Source dataset
uspto-grants-2002_04
Patent number
US06380194B1

Reaction notes

Loading…