Trifluoroacetic acid → HCID 70665158, compound

HRID 1403570Notes

Reaction equation

HRID 1403570 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[N:16][C:17]3[C:22]([N:23]=2)=[CH:21][C:20]([C:24]([O:26]C)=[O:25])=[CH:19][CH:18]=3)[C@@H:10]([CH3:35])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>ClCCl.O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:15]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]3[CH3:35])=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:24]([OH:26])=[O:25])[CH:21]=3)[N:16]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 70664893HCID 70664893, compound

Product 1

HCID 70665158HCID 70665158, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-[(2S)-4-[(tert-butoxy)carbonyl]-2-methylpiperazin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate (260 mg, 0.54 mmol) in dichloromethane (30 mL) was added CF3COOH (2 mL). The resulting solution was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in methanol (15 mL), and sodium hydroxide (20 mg, 0.50 mmol) in water (1 mL) was added. The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (3 mL), the pH adjusted to 6, and the resulting solution concentrated in vacuo. The crude product (40 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC(MS-Directed)): Column, 1#-PrepC-001(XBridge Shield RP18 19*150 186002987 111130103113 03), N; mobile phase, WATER WITH 0.03% NH3H2O and CH3CN (10% CH3CN up to 22% in 7 min, hold 100% in 2 min, hold 10% in 2 min); Detector, UV 220 nm) to afford 2-(4-fluorophenyl)-3-[(2S)-2-methylpiperazin-1-yl]quinoxaline-6-carboxylic acid as a yellow solid (31 mg, 59%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol (15 mL)
  3. stirringThe resulting solution was stirred overnight at room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in water (3 mL)
  6. concentrationthe resulting solution concentrated in vacuo
  7. customThe crude product (40 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC(MS-Directed))
  8. waitmobile phase, WATER WITH 0.03% NH3H2O and CH3CN (10% CH3CN up to 22% in 7 min
  9. customin 2 min
  10. customin 2 min

Sources & evidence

ORD record
ord-150b15d5eb7042d1b8c820ea81ba67ec
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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