Triethylamine → n-(2-(Dimethylamino)ethyl)-n-methyl-4-(3-(quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide

HRID 15986

Reaktionsgleichung

Reaktionsgleichung von HRID 15986
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]1[C:34]2[C:29](=[CH:30][C:31]([CH2:35][N:36]3[C:44]4[C:39](=[N:40][CH:41]=[C:42]([C:45]5[CH:53]=[CH:52][C:48]([C:49]([OH:51])=O)=[CH:47][CH:46]=5)[N:43]=4)[N:38]=[N:37]3)=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.[CH3:54][N:55]([CH3:60])[CH2:56][CH2:57][NH:58][CH3:59].C(N(CC)CC)C>CN(C=O)C>[CH3:54][N:55]([CH3:60])[CH2:56][CH2:57][N:58]([CH3:59])[C:49](=[O:51])[C:48]1[CH:47]=[CH:46][C:45]([C:42]2[N:43]=[C:44]3[N:36]([CH2:35][C:31]4[CH:30]=[C:29]5[C:34](=[CH:33][CH:32]=4)[N:25]=[CH:26][CH:27]=[CH:28]5)[N:37]=[N:38][C:39]3=[N:40][CH:41]=2)=[CH:53][CH:52]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593418624-(3-(Quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzoic acid

Produkt 1

HCID 45381021n-(2-(Dimethylamino)ethyl)-n-methyl-4-(3-(quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamideAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (82 mg, 0.22 mmol) was added to a mixture of 4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzoic acid (75 mg, 0.20 mmol), N1,N1,N2-trimethylethane-1,2-diamine (22 mg, 0.22 mmol) and triethylamine (0.060 mL, 0.43 mmol) in DMF (2.0 mL). After stirring for 18 hours, the reaction was partitioned between dichloromethane:ethanol (9:1) and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated by rotary evaporation to afford 108 mg of crude material. The material was purified by pre-HPLC to give N-(2-(dimethylamino)ethyl)-N-methyl-4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide (54 mg, yield 48%).

Aufarbeitung

  1. customthe reaction was partitioned between dichloromethane:ethanol (9:1) and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto afford 108 mg of crude material
  7. customThe material was purified by pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ca7cbd2bacca4b64818d67886f66b7f8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

Verknüpfte Notizen

Wird geladen…