Trifluoroacetic acid → HCID 21961390, compound

HRID 887604Notes

Reaction equation

HRID 887604 reaction equation
C([C:8]1[CH:33]=[CH:32][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])=[C:17]([O:28][CH2:29][CH2:30][NH2:31])[CH:16]=2)=[O:13])=[C:10]([Cl:34])[N:9]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:31][CH2:30][CH2:29][O:28][C:17]1[CH:16]=[C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:32]=[CH:33][CH:8]=[N:9][C:10]=2[Cl:34])[CH:20]=[CH:19][C:18]=1[C:21]([F:26])([F:27])[C:22]([F:25])([F:24])[F:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588703HCID 86588703, compound

Product 1

HCID 21961390HCID 21961390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 500 mg (0.98 mmol) Boc-N-[3-(2-Amino-ethoxy)-4-pentafluoroethyl-phenyl]-2-chloro-nicotinamide in 10 ml CH2Cl2 was added 10 ml TFA and stirred for 2 h. The reaction was concentrated down, treated with 6N aqueous NaOH, and extracted 3 times with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered, concentrated down, and dried under vacuum, yielding the titled compound.

Workup

  1. concentrationThe reaction was concentrated down
  2. additiontreated with 6N aqueous NaOH
  3. extractionextracted 3 times with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e205afbf6b5146719f06069cfb6f5298
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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