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

HRID 25052

Reaktionsgleichung

Reaktionsgleichung von HRID 25052
[H-].[Na+].C(#[N:5])C.[NH2:6][C:7]1[N:12]=[C:11]([CH2:13][C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])[N:10]=[C:9]([NH:22][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[N:8]=1.Cl[CH2:32][CH2:33][CH2:34][N:35]=[C:36]=[O:37]>O1CCOCC1.CN1CCCC1=O>[C:27]([C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:9]2[N:10]=[C:11]([CH2:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[N:12]=[C:7]([NH:6][CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:5])=[O:37])[N:8]=2)=[CH:30][CH:29]=1)#[N:28]

Komponenten

7

Edukt 4

HCID 6342Acetonitrile2×HCID 24758Sodium hydrideHCID 166752Propane, 1-chloro-3-isocyanato-HCID 4863624-[[4-Amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Produkt 1

HCID 5054153-[[4-(4-Cyanoanilino)-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]propylureaAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Sodium hydride (0.00150 mol), ACN (5 ml), compound (1) (0.00135 mol) in 1,4-dioxane (10 ml), and ACN (10 ml) were combined under argon. The solution was stirred for 1 hour. 1-chloro-3-isocyanato-propane (0.00137 mol) was added. The reaction mixture was stirred for 1 hour. 1-methyl-pyrrolidinone (10 ml) was added. The reaction mixture was stirred for 16 hours. Then, the mixture was concentrated. The concentrate was partitioned between DCM/H2O. The resulting solution was filtered, dried over K2CO3, filtered, concentrated and the residue was treated with NH3 in 1,4-dioxane (12 ml, 0.5 M) and heated under pressure at 55° C. The resulting solution was concentrated and further purified by flash column chromatography (eluent: DCM/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 0.12 g (18.9%) of N-[3-[[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl) methyl]-1,3,5-triazin-2-yl]amino]propyl]urea (compound 23).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 1 hour
  2. stirringThe reaction mixture was stirred for 16 hours
  3. concentrationThen, the mixture was concentrated
  4. customThe concentrate was partitioned between DCM/H2O
  5. filtrationThe resulting solution was filtered
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionthe residue was treated with NH3 in 1,4-dioxane (12 ml, 0.5 M)
  10. concentrationThe resulting solution was concentrated
  11. customfurther purified by flash column chromatography (eluent: DCM/CH3OH 95/5)
  12. customThe pure fractions were collected
  13. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fc5de1ee83c64d94a8e2e2ff7505a07c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858609B2

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