Trifluoroacetic anhydride → Sch 28080

HRID 544462Notes

Reaction equation

HRID 544462 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][C:20]([NH2:22])=O)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][C:20]#[N:22])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 204590208-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-acetamide

Product 1

HCID 108137Sch 28080

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of 8-benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-acetamide (3 g) in dioxane was cooled to 5°-10° C. To the suspension there was added over a period of 5 minutes a solution of trifluoroacetic anhydride (6 g) in dioxane. The mixture was maintained cool and stirred for 30 minutes. Thereafter the mixture was allowed to warm to room temperature and was stirred for a further four hours. The mixture was thendiluted with ice water and the precipitate was filtered. After recrystallization from ethylacetate the desired compound was obtained (m.p. 163°-166° C.).

Workup

  1. temperaturewas cooled to 5°-10° C
  2. temperatureThe mixture was maintained
  3. temperaturecool
  4. stirringwas stirred for a further four hours
  5. filtrationthe precipitate was filtered
  6. customAfter recrystallization from ethylacetate the desired compound
  7. customwas obtained (m.p. 163°-166° C.)

Sources & evidence

ORD record
ord-db7c1d386efc40718e5dbb3d44255569
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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