p-Toluenesulfonic acid → HCID 24992532, compound

HRID 1914740Notes

Reaction equation

HRID 1914740 reaction equation
[F:1][C:2]([F:37])([F:36])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[N:20]=[CH:19][C:18]2[CH2:17][CH2:16][C:15]3[C:21]([C:33]([NH2:35])=[O:34])=[N:22][N:23]([CH2:24][CH2:25][O:26]C4CCCCO4)[C:14]=3[C:13]=2[N:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[F:37][C:2]([F:1])([F:36])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[N:20]=[CH:19][C:18]2[CH2:17][CH2:16][C:15]3[C:21]([C:33]([NH2:35])=[O:34])=[N:22][N:23]([CH2:24][CH2:25][OH:26])[C:14]=3[C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59454364HCID 59454364, compound

Product 1

HCID 24992532HCID 24992532, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.085 g (0.15 mmol) of 8-(2-trifluoromethoxy-phenylamino)-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide were dissolved in 10 mL of ethanol and 28 mg of p-toluensulfonic acid (0.15 mmol) were added. The solution was stirred at room temperature overnight and the solvent removed in vacuo. The residue was purified by flash chromatography on silica gel (eluant: ethyl acetate/hexane 80/20) to afford 59 mg (90% yield) of the title compound.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (eluant: ethyl acetate/hexane 80/20)

Sources & evidence

ORD record
ord-10cd2190fa7c407584f4f76e2434434e
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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