Water → 5-cyano-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}furan-2-sulfonamide

HRID 1024922Notes

Reaction equation

HRID 1024922 reaction equation
[C:1]([C:3]1[O:7][C:6]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:18][C@H:19]([CH3:41])[CH2:20][O:21]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:15]=[C:14]([S:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[C:45]=3[F:51])[N:13]=2)(=[O:10])=[O:9])=[CH:5][CH:4]=1)#[N:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(OC)C=CC=CC=1.O>CO>[C:1]([C:3]1[O:7][C:6]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:18][C@H:19]([CH3:41])[CH2:20][OH:21])[N:15]=[C:14]([S:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[C:45]=3[F:51])[N:13]=2)(=[O:10])=[O:9])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 536283685-cyano-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(triphenylmethyloxy)ethoxy]pyrimidin-4-yl}furan-2-sulfonamide

Product 1

HCID 595588135-cyano-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}furan-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-cyano-N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(triphenylmethyloxy)ethoxy]pyrimidin-4-yl}furan-2-sulfonamide (the product of step ii) (0.15 g) in methanol (5 mL) was added para-toluenesulfonic acid hydrate (39 mg) and anisole (0.23 mL). After stirring at room temperature for 5 h, H2O (5 mL) was added and the mixture extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4), filtered and evaporated to dryness in vacuo. The resulting crude solid was purified by reverse phase HPLC (75% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent) to give the title compound as a white solid. Yield: 20 mg.

Workup

  1. extractionthe mixture extracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThe resulting crude solid was purified by reverse phase HPLC (75% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent)

Sources & evidence

ORD record
ord-f9d0750f60c743e7862501754e72c4c7
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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