Triethylamine → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide

HRID 79434Notes

Reaction equation

HRID 79434 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH2:33]([C:35]1[C:43]2[C:42]([NH2:44])=[CH:41][CH:40]=[CH:39][C:38]=2[N:37]([CH2:45][C:46]2[CH:50]=[CH:49][N:48]([CH2:51][CH3:52])[N:47]=2)[N:36]=1)[CH3:34]>CN1CCCC1=O>[CH2:33]([C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][C:42]=2[NH:44][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:13])[N:37]([CH2:45][C:46]2[CH:50]=[CH:49][N:48]([CH2:51][CH3:52])[N:47]=2)[N:36]=1)[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 672598083-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amineHCID 672607377-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67259540N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (Preparation I; 224 mg, 1.25 mmol) was dissolved in anhydrous N-methylpyrrolidinone (0.2 M) and treated with triethylamine (0.35 mL, 2.5 mmol). When the mixture was homogeneous 2,4,6-trichlorobenzoyl chloride (0.20 mL, 1.31 mmol) was added dropwise. The mixture was stirred for 30 minutes at ambient temperature. 3-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (0.30 mg, 1.11 mmol) was added in one portion and the sides of the flask were washed with anhydrous N-methylpyrrolidinone (2 mL). The mixture was heated to 90° C. and stirred for 16 hours. The mixture was allowed to cool and filtered through GF/F paper washing with ethyl acetate. The filtrate was concentration under reduced pressure and diluted with water to give a beige precipitate which was collected by filtration, washed with water and dried under high vacuum to give N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (259 mg). MS m/z 432.1 (M+1, APCI+).

Workup

  1. additionwas added dropwise
  2. washthe sides of the flask were washed with anhydrous N-methylpyrrolidinone (2 mL)
  3. temperatureThe mixture was heated to 90° C.
  4. stirringstirred for 16 hours
  5. temperatureto cool
  6. filtrationfiltered through GF/F paper
  7. washwashing with ethyl acetate
  8. concentrationconcentration under reduced pressure
  9. additiondiluted with water
  10. customto give a beige precipitate which
  11. filtrationwas collected by filtration
  12. washwashed with water
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-aedc2a0452fc4b4198ce953fb40ed17b
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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