Trifluoroacetic acid → N-{5-[3-(1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide

HRID 734972Notes

Reaction equation

HRID 734972 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([C:17]3[CH:26]=[C:25]4[C:20]([N:21]=[CH:22][C:23]([N:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[N:24]4)=[CH:19][CH:18]=3)[CH:14]=[N:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(#N)C>[N:27]1([C:23]2[CH:22]=[N:21][C:20]3[C:25]([N:24]=2)=[CH:26][C:17]([C:13]2[CH:12]=[C:11]([NH:10][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:16]=[N:15][CH:14]=2)=[CH:18][CH:19]=3)[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578433121,1-Dimethylethyl 4-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)-1-piperazinecarboxylate

Product 1

HCID 57843497N-{5-[3-(1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)-1-piperazinecarboxylate (1.80 mmol) in acetonitrile (4 ml) was added concentrated trifluoroacetic acid (4 ml). The reaction stirred at ambient temperature for 18 hours and was then concentrated to an orange oil. The residue was neutralized with 10% sodium carbonate solution and purified on silica by column chromatography (15% methanol/ethyl acetate). The desired fractions were combined and concentrated to give the title compound (500 mg, 61%) as a tan solid. MS(ES)+ m/e 447.2 [M+H]+.

Workup

  1. concentrationwas then concentrated to an orange oil
  2. custompurified on silica by column chromatography (15% methanol/ethyl acetate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bb35c467db6145c2bf7376fdc3b05acb
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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