p-Toluenesulfonic acid → HCID 178440663, compound

HRID 1893457Notes

Reaction equation

HRID 1893457 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[N:14]3[C:15]4[C:20]([N:21]=[C:22]([NH:23][CH2:24][CH2:25][CH2:26][O:27]C5CCCCO5)[C:13]3=[N:12][CH:11]=2)=[CH:19][C:18]([C:34]([F:37])([F:36])[F:35])=[CH:17][CH:16]=4)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[N:14]3[C:15]4[C:20]([N:21]=[C:22]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[C:13]3=[N:12][CH:11]=2)=[CH:19][C:18]([C:34]([F:36])([F:35])[F:37])=[CH:17][CH:16]=4)[NH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178440662HCID 178440662, compound

Product 1

HCID 178440663HCID 178440663, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-tert-butyl-1H-pyrazol-5-yl)-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-amine (11 mg, 0.021 mmol) in methanol (0.2 mL) cooled at 0° C. was added para-toluenesulfonic acid (9 mg, 0.047 mmol). The mixture was stirred at room temperature under argon for 5 h and then concentrated in vacuo. The residue is diluted in ethyl acetate and water. The aqueous layer is basified to pH 8 with a saturated aqueous solution of sodium hydrogenocarbonate and extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1) to afford the title compound (7 mg, 78%) as a colourless gum.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted in ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-3c80be3bff7248cb95319f801ccd4712
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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