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

HRID 25049
Notes
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Reaction equation

HRID 25049 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 31275
1,4-Dioxane
Solvent

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-d61f51406e084b97a43f42bf73cd41db
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes