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

HRID 1175427Notes

Reaction equation

HRID 1175427 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-617ea1e63e1b45d4ade0d1415f3405d3
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

Loading…