Trifluoroacetic anhydride → HCID 57901755, compound

HRID 1851346Notes

Reaction equation

HRID 1851346 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([NH2:21])=O)=[CH:15]2)(=[O:8])=[O:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8])#[N:21]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 57476167HCID 57476167, compound

Product 1

HCID 57901755HCID 57901755, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (4.65 g) and pyridine (20 mL) was slowly added trifluoroacetic anhydride (4.50 mL) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography, and eluted with tetrahydrofuran-hexane (2:3, volume ratio). The eluate was treated with activated carbon and concentrated to give the title compound (4.04 g, yield 92%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point 283-284° C.

Workup

  1. customat 0° C.
  2. concentrationThe reaction mixture was concentrated
  3. addition10% aqueous citric acid solution was added
  4. filtrationthe resulting crystals were filtrated
  5. washwashed with water
  6. customdried
  7. washeluted with tetrahydrofuran-hexane (2:3, volume ratio)
  8. additionThe eluate was treated with activated carbon
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cda5f657b65a4009acf0d2644afd8497
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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