Trifluoroacetic acid → HCID 25122618, compound

HRID 734957Notes

Reaction equation

HRID 734957 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:20]=[C:19]3[C:14]([N:15]=[CH:16][C:17]([N:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[N:9][CH:10]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>C(#N)C>[N:21]1([C:17]2[CH:16]=[N:15][C:14]3[C:19]([N:18]=2)=[CH:20][C:11]([C:7]2[CH:6]=[C:5]([S:2]([NH2:1])(=[O:4])=[O:3])[CH:10]=[N:9][CH:8]=2)=[CH:12][CH:13]=3)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57843350HCID 57843350, compound

Product 1

HCID 25122618HCID 25122618, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{7-[5-(aminosulfonyl)-3-pyridinyl]-2-quinoxalinyl}-1-piperazinecarboxylate (0.21 mmol) (prepared according to Scheme 1) in acetonitrile (4 mL) was treated with concentrated trifluoroacetic acid (4 mL) for 2 hours. The reaction mixture was then concentrate and neutralized with saturated sodium bicarbonate (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to yield the title product. MS(ES)+ m/e 371.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrate
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d86cb2289da74f13b269b1898878b48c
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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