Triethylamine → HCID 68818057, compound

HRID 729483Notes

Reaction equation

HRID 729483 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]2[N:10]=[CH:11][C:12]([C:15]([NH2:17])=O)=[N:13][CH:14]=2)[CH2:6]1.C(N(CC)CC)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:17])=[N:13][CH:14]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 45380634HCID 45380634, compound

Product 1

HCID 68818057HCID 68818057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-[3-(2-bromo-5-fluorophenoxy)azetidin-1-yl]pyrazine-2-carboxamide (0.66 g, 1.8 mmol) in THF (30 mL) at 0° C. was added triethylamine (0.46 g, 4.5 mmol) followed by TFAA (0.57 g, 2.7 mmol). After 15 min at room temperature, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was separated, dried over sodium sulfate and filtered. The residue was purified by flash chromatography to provide the title compound as a white solid.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bd11816ae055421e85d8aba7baf1165c
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

Loading…