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

Reaction equation

HRID 15986 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 45381021n-(2-(Dimethylamino)ethyl)-n-methyl-4-(3-(quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-ca7cbd2bacca4b64818d67886f66b7f8
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

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