Triethylamine → HCID 68819220, compound

HRID 729453Notes

Reaction equation

HRID 729453 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]([NH2:19])=O)=[N:15][CH:16]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:19])=[N:15][CH:16]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 690622895-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide

Product 1

HCID 68819220HCID 68819220, compound

Procedure

To a suspension of 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide from Step 4 (1.65 g, 4.17 mmol) in TBF (50 mL) at 0° C. was added triethylamine (1.45 mL, 10.5 mmol) followed by trifluoroacetic anhydride (0.885 mL, 6.26 mmol). After a period of 10 min at 0° C., the reaction mixture was raised gradually to room temperature. The mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, dried over sodium sulfate and evaporated. The crude mixture was purified by flash chromatography (35% ethyl acetate in hexane) to provide the title compound.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude mixture was purified by flash chromatography (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-928bd42788174a00a6b2e0288675f414
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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