Triethylamine → HCID 22637225, compound

HRID 2416015Notes

Reaction equation

HRID 2416015 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:13][NH2:14])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[Br:22][CH:23]([CH3:27])[C:24](O)=[O:25].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[Cl:2][C:3]1[C:4]([CH2:13][NH:14][C:24](=[O:25])[CH:23]([Br:22])[CH3:27])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 117292-Bromopropionic acidHCID 682631,1'-CarbonyldiimidazoleHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine hydrochloride

Product 1

HCID 22637225HCID 22637225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine hydrochloride (1.0 g) in tetrahydrofuran (5 ml) and triethylamine (0.41 g) which had been stirred at room temperature for 30 minutes, was added a mixture of 2-bromopropionic acid (0.62 g) and carbonyldiimidazole (0.65 g) in tetrahydrofuran (5 ml) which had also been stirred at room temperature for 30 minutes. The combined mixture was stirred at room temperature for 12 hours and then the solvent was removed. The residue was partitioned between diethyl ether and water and the layers separated. The organic phase was dried (MgSO4) and the solvent removed to give the title product.

Workup

  1. additionwas added
  2. stirringhad also been stirred at room temperature for 30 minutes
  3. stirringThe combined mixture was stirred at room temperature for 12 hours
  4. customthe solvent was removed
  5. customThe residue was partitioned between diethyl ether and water
  6. customthe layers separated
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customthe solvent removed

Sources & evidence

ORD record
ord-96915c72a821405999a05fa3782ac12e
Source dataset
uspto-grants-2004_11
Patent number
US06821992B1

Reaction notes

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