p-Toluenesulfonic acid → HCID 11591385, compound

HRID 1024869Notes

Reaction equation

HRID 1024869 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:29][C@H:30]([CH3:52])[CH2:31][O:32]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(OC)C=CC=CC=1>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=2)(=[O:19])=[O:20])[CH:14]=[C:13]([O:29][C@H:30]([CH3:52])[CH2:31][OH:32])[N:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7519AnisoleHCID 67051259HCID 67051259, compound

Product 1

HCID 11591385HCID 11591385, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-4-pyrimidinyl]-1,6-dihydro-1-methyl-6-oxo-3-pyridinesulfonamide (the product from step (0.16 g) in MeOH (10 mL) was added p-toluenesulfonic acid (50 mg) and anisole (0.22 g). The reaction was then stirred at room temperature for 18 h. The reaction was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous layer was then further extracted with EtOAc (2×100 mL). Combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by reverse phase HPLC using TFA (0.2%)/MeCN to give a white solid. Yield: 9 mg.

Workup

  1. customThe reaction was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. extractionThe aqueous layer was then further extracted with EtOAc (2×100 mL)
  3. dry with materialCombined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by reverse phase
  7. customto give a white solid

Sources & evidence

ORD record
ord-a2308685d21f4575a5660c947b27776b
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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