Glycinamide → 2-[[4-(4-Cyanoanilino)-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]acetamide

HRID 270629

Reaction equation

HRID 270629 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]=1.[NH2:26][CH2:27][C:28]([NH2:30])=[O:29].C(N(CC)C(C)C)(C)C>O1CCOCC1>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:4]2[N:5]=[C:6]([CH2:8][C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[N:7]=[C:2]([NH:26][CH2:27][C:28]([NH2:30])=[O:29])[N:3]=2)=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 3

HCID 69020GlycinamideHCID 81531DiisopropylethylamineHCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 5054092-[[4-(4-Cyanoanilino)-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]acetamideYield 41.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Intermediate (27) (0.00423 mol), 2-amino-acetamide (0.00431 mol), 1,4-dioxane (20 ml) and N,N-diisopropylethylamine (0.00862 mol) were combined and stirred at RT for 16 hours under argon. The reaction mixture was quenched with H2O and filtered. The residue was washed with H2O, filtered and recrystallized from ACN (200 ml). The precipitate was filtered off and dried, yielding 0.75 g (41.4%) of [N-[4-[(4-cyano-phenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]]aminoacetamide (compound 14).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. filtrationfiltered
  3. washThe residue was washed with H2O
  4. filtrationfiltered
  5. customrecrystallized from ACN (200 ml)
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-0753b49a9b6f4d88adca9743065e65cd
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Linked notes

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