Dimethyl Sulfoxide → HCID 178522583, compound

HRID 855550Notes

Reaction equation

HRID 855550 reaction equation
[CH:1]1([CH2:6][CH:7]([C:16]2[CH:17]=[N:18][C:19](F)=[CH:20][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[S:24](C)=O>>[CH:1]1([CH2:6][CH:7]([C:16]2[CH:17]=[N:18][C:19]([SH:24])=[CH:20][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 10245400HCID 10245400, compound

Product 1

HCID 178522583HCID 178522583, compound

Conditions

Temperature
160 °C

Procedure

A solution of 3-cyclopentyl-2-(6-fluoropyridin-3-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 14, 350 mg, 1.1 mmol) and NaSMe (1.53 g, 22.0 mmol) in anhydrous, degassed DMSO (4 mL) was stirred at 160° C. (bath) for 1 h. On cooling, the mixture was partitioned between EtOAc (50 mL) and 1M HCl (50 mL). The organic layer was washed with H2O (20 mL) and brine (50 mL). The solvent was evaporated and the residue recrystallised (EtOAc-1H) to give the title compound: RTA=3.24 min; m/z (ES+)=334.2 [M+H]+.

Workup

  1. temperatureOn cooling
  2. customthe mixture was partitioned between EtOAc (50 mL) and 1M HCl (50 mL)
  3. washThe organic layer was washed with H2O (20 mL) and brine (50 mL)
  4. customThe solvent was evaporated
  5. customthe residue recrystallised (EtOAc-1H)

Sources & evidence

ORD record
ord-0242924dac164d60967db9788bb696db
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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