Diisopropylethylamine → N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

HRID 1510956

Reaktionsgleichung

Reaktionsgleichung von HRID 1510956
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([OH:19])=O)[CH2:12]2)[N:3]=1.C(N(C(C)C)CC)(C)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][NH2:37])=[C:32]([Cl:38])[CH:31]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>CN(C)C=O>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][NH:37][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][CH:11]([NH:10][C:4]3[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:8][CH3:9])[N:5]=3)[CH2:12]2)=[O:19])=[C:32]([Cl:38])[CH:31]=1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 25258775(4-Bromo-2-chlorophenyl)methanamineHCID 594482213-{[4-Methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid

Produkt 1

HCID 67493540N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxylic acid (0.324 g, 0.855 mmol) in N,N-Dimethylformamide (DMF) (25 ml) was added diisopropylethylamine (0.329 ml, 1.881 mmol) followed by 1-(4-bromo-2-chlorophenyl)methanamine (0.286 g, 0.855 mmol) and 1H-1,2,3-benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.416 g, 0.940 mmol). The reaction was stirred at room temperature for 3 hours. Saturated NaHCO3 was added to the reaction, at which time white solids precipitated from solution. The solids were filtered, washed with acetonitrile, and dried to provide N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (160 mg, 0.34 mmol, 40%). MS (ES+): m/e 467, 469 [M+H]+.

Aufarbeitung

  1. customprecipitated from solution
  2. filtrationThe solids were filtered
  3. washwashed with acetonitrile
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-09a6be4800b744cca1fb23ff7da90506
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212032B2

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