Trifluoroacetic acid → HCID 117667244, compound

HRID 1526179Notes

Reaction equation

HRID 1526179 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:14]([C:15](=[O:17])[NH2:16])=[N:13][CH:12]=[C:11]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)[N:10]=2)[CH:5]=[CH:4][C:3]=1[N:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1.FC(F)(F)C(O)=O>ClCCCl>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:14]([C:15]([NH2:16])=[O:17])=[N:13][CH:12]=[C:11]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)[N:10]=2)[CH:5]=[CH:4][C:3]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667006HCID 117667006, compound

Product 1

HCID 117667244HCID 117667244, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of tert-butyl 4-(2-bromo-4-{[3-carbamoyl-6-(3-nitrophenoxy)pyrazin-2-yl]amino}phenyl)piperazine-1-carboxylate (682 mg) and 1,2-dichloroethane (7 mL) was added trifluoroacetic acid (3 mL) under ice-cooling, and followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, then diluted with chloroform, and neutralized with a 10% aqueous potassium carbonate solution. After extracting with chloroform, the organic phase was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3-{[3-bromo-4-(piperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (523 mg) as a yellow amorphous substance.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with chloroform
  4. extractionAfter extracting with chloroform
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aa3c4ce24ec641b3808bdbffb37b30b7
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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