HCID 178503223, compound → HCID 178503207, compound

HRID 724336Notes

Reaction equation

HRID 724336 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[N:19][C:18]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([S:31][CH3:32])[CH:26]=2)[CH2:11][CH2:10]1)=[O:7]>CN(C)C=O>[F:23][C:21]1[CH:20]=[N:19][C:18]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([S:31][CH3:32])[CH:26]=2)=[C:17]([CH:22]=1)[C:16]([NH:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([N:8]2[CH2:2][CH2:3][CH2:4][CH2:5][C:6]2=[O:7])[CH2:10][CH2:11]1)=[O:33]

Participants

3

Reactant 1

HCID 178503223HCID 178503223, compound

Product 1

HCID 178503207HCID 178503207, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-N-{4-[(5-Chloropentanoyl)amino]cyclohexyl}-5-fluoro-2-[3-(methylsulfanyl)phenoxy]nicotinamide (220 mg, 0.405 mmol) was dissolved in dimethylformamide (5 ml) sodium hydride 60% dispersion in oil (41 mg, 1.01 mmol) was added. The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium hydrogen carbonate solution (10 ml) and dichloromethane (15 ml) and the aqueous phase was extracted with dichloromethane (3×15 ml). The combined organic extracts were washed with water (2×10 ml), brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was triturated with diethylether (5 ml) to give the title compound (78 mg) as a white solid.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between sat. sodium hydrogen carbonate solution (10 ml) and dichloromethane (15 ml)
  4. extractionthe aqueous phase was extracted with dichloromethane (3×15 ml)
  5. washThe combined organic extracts were washed with water (2×10 ml), brine (10 ml)
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was triturated with diethylether (5 ml)

Sources & evidence

ORD record
ord-bced46492d90478bb0152878193f1bdf
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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