Triethylamine → HCID 57384340, compound

HRID 706671Notes

Reaction equation

HRID 706671 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]2[CH:7]=1.C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[NH2:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1[CH:40]=[N:41][N:42]2[CH2:47][C:48]1[CH:49]=[C:50]([CH:55]=[CH:56][CH:57]=1)[C:51]([O:53][CH3:54])=[O:52]>CCOC(C)=O.CN1C(=O)CCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([NH:37][C:38]3[CH:46]=[CH:45][CH:44]=[C:43]4[C:39]=3[CH:40]=[N:41][N:42]4[CH2:47][C:48]3[CH:49]=[C:50]([CH:55]=[CH:56][CH:57]=3)[C:51]([O:53][CH3:54])=[O:52])=[O:17])=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 67976218HCID 67976218, compound

Product 1

HCID 57384340HCID 57384340, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a vial was added 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (0.260 g, 1.05 mmol) and NMP (3.5 mL). Triethylamine (0.243 mL, 1.74 mmol) was added and the mixture was stirred until homogeneous. 2,4,6-Trichlorobenzoyl chloride (0.153 mL, 0.975 mmol) was added and the mixture was stirred at ambient temperature for 0.5 hours. Methyl 3-((4-amino-1H-indazol-1-yl)methyl)benzoate (0.196 g, 0.697 mmol) was added as a NMP solution (1.2 mL), and the reaction mixture was sealed in the vial and warmed to 80° C. with stirring overnight. The reaction mixture was cooled and diluted with EtOAc (20 mL), and then filtered to remove white solids. The solids were washed with EtOAc and the filtrate was concentrated under vacuum until only DMA was left. The concentrated solution diluted with water/saturated aqueous NaHCO3 (25 mL, 1:1) forming a precipitate. The precipitate was isolated by filtration and the solid was washed with water, Et2O, and hexanes, then dried under vacuum at 40° C. for 4 hours to provide 0.279 g (74%) of the title compound. MS (ES+APCI) m/z=500 (M+H).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 0.5 hours
  2. customthe reaction mixture was sealed in the vial and
  3. stirringwith stirring overnight
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. customto remove white solids
  7. washThe solids were washed with EtOAc
  8. concentrationthe filtrate was concentrated under vacuum until only DMA
  9. waitwas left
  10. additionThe concentrated solution diluted with water/saturated aqueous NaHCO3 (25 mL, 1:1)
  11. customforming a precipitate
  12. customThe precipitate was isolated by filtration
  13. washthe solid was washed with water, Et2O, and hexanes
  14. customdried under vacuum at 40° C. for 4 hours

Sources & evidence

ORD record
ord-e96945e693714ef0bd200c7b0fdaca33
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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