Trifluoroacetic acid → HCID 22710436, compound

HRID 352814Notes

Reaction equation

HRID 352814 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:27][C:28]([OH:30])=O)=O)(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:43][S:44]([NH2:47])(=[O:46])=[O:45].C1CCN2C(=NCCC2)CC1.[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62]>O1CCCC1.C(Cl)Cl>[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62].[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:27][C:28]([NH:47][S:44]([CH3:43])(=[O:46])=[O:45])=[O:30])[CH2:10]1)(=[O:16])=[O:15])=[CH:25]2

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22709504HCID 22709504, compound

Product 1

HCID 22710436HCID 22710436, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (5 ml) was dissolved 1-(tert-butoxycarbonyl)-2-[(carboxy)methyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (772 mg), followed by the addition of carbonyldiimidazole (820 mg). The resulting mixture was heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was added with methanesulfonamide (322 mg) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.50 ml), followed by stirring overnight. The reaction mixture was concentrated under reduced pressure. To the residue was added a 1N aqueous solution of hydrochloric acid. After removal of the supernatant, the precipitate was washed with water and dried, whereby a colorless foam was obtained. The substance was dissolved in methylene chloride (10 ml), followed by the addition of trifluoroacetic acid (10 ml). The resulting mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure. Diethyl ether was added to the residue and the precipitate thus obtained was collected by filtration, whereby the title compound (863 mg) was obtained as a colorless solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue was added a 1N aqueous solution of hydrochloric acid
  5. customAfter removal of the supernatant
  6. washthe precipitate was washed with water
  7. customdried
  8. customwhereby a colorless foam was obtained
  9. stirringThe resulting mixture was stirred at room temperature for 10 minutes
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. additionDiethyl ether was added to the residue
  12. customthe precipitate thus obtained
  13. filtrationwas collected by filtration, whereby the title compound (863 mg)
  14. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-066c5085bd6845b4967205e0e79a2360
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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