HCID 874532, compound → HCID 69748795, compound

HRID 1062376Notes

Reaction equation

HRID 1062376 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13].I[C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C[O-].[Na+]>CC(N(C)C)=O.[Cu]Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:20]2[CH:25]=[CH:24][C:23]([S:26]([N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:13])[F:14]

Participants

6

Reactant 3

HCID 874532HCID 874532, compoundHCID 10942334Sodium MethoxideHCID 54333950HCID 54333950, compound

Product 1

HCID 69748795HCID 69748795, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

Copper (1) chloride (0.038 g) was added to a mixture of (R)-N-(2-chloro-4-mercaptophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 210) (0.21 g), N-(4-iodobenzenesulphonyl)pyrrolidine (0.258 g) and sodium methoxide (0.042 g) in DMA (5 ml). The mixture was heated at 150° C. with stirring for 4 hours then cooled and the DMA removed by evaporation. Ethyl acetate (20 ml) and water (20 ml) was added and the mixture was filtered. The aqueous layer was extracted with ethyl acetate (3×20 ml) and the organic layers were combined and dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column, eluting with methanol/DCM 0-10% to give the title compound (0.16 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 1.75-1.85 (m, 4H), 3.2-3.3 (m, 4H), 4.0 (s, 1H), 7.2-7.3 (m, 2H), 7.4-7.45 (m, 1H), 7.6 (s, 1), 7.7 (d, 2H), 8.45 (d, 1H), 9.15 (s, 1H); MS (ESP−): 507.

Workup

  1. temperaturethen cooled
  2. customthe DMA removed by evaporation
  3. additionEthyl acetate (20 ml) and water (20 ml) was added
  4. filtrationthe mixture was filtered
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×20 ml)
  6. customdried
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified on a silica gel Mega Bond Elut column
  9. washeluting with methanol/DCM 0-10%

Sources & evidence

ORD record
ord-acd0253acaae4a3d8aaba5c09bd405f7
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

Loading…