Trifluoroacetic acid → HCID 57843470, compound

HRID 734977Notes

Reaction equation

HRID 734977 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:17]=[N:16][C:15]3[C:10](=[CH:11][C:12]([C:18]4[CH:19]=[N:20][CH:21]=[C:22]([NH:24][S:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)(=[O:27])=[O:26])[CH:23]=4)=[CH:13][CH:14]=3)[N:9]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:8]1[CH:17]=[N:16][C:15]2[C:10]([N:9]=1)=[CH:11][C:12]([C:18]1[CH:23]=[C:22]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:21]=[N:20][CH:19]=1)=[CH:13][CH:14]=2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57843282HCID 57843282, compound

Product 1

HCID 57843470HCID 57843470, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-oxo-4-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)-1-piperazinecarboxylate (0.21 mmol) in acetonitrile (4 ml) was added concentrated trifluoroacetic acid (4 ml). The reaction stirred at ambient temperature for 1 hour and was then concentrated to an orange oil. The residue was neutralized with saturated sodium bicarbonate solution upon which a precipitate formed. The precipitate was dissolved in ethyl acetate and crashed out of solution with hexanes, which was filtered and dried to afford the title compound (66 mg, 67%) as an off-white solid. MS(ES)+ m/e 461.2 [M+H]+.

Workup

  1. concentrationwas then concentrated to an orange oil
  2. customformed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-53e776d5a3f84772921eb0a87ae2e5d0
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

Loading…