Isopropanol → Ammonia

HRID 724342Notes

Reaction equation

HRID 724342 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21](SC)[CH:20]=2)=[C:6]([CH:17]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1)=[O:8].O[O:28][S:29]([O-:31])=O.[K+].[CH:33](O)(C)C>O1CCCC1.O>[NH3:4].[F:1][C:2]1[CH:3]=[N:4][C:5]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([S:29]([CH3:33])(=[O:31])=[O:28])[CH:24]=2)=[C:6]([CH:17]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1)=[O:8]

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 23707502Potassium hydroxy sulfiteHCID 178503228HCID 178503228, compound

Product 2

HCID 222AmmoniaHCID 178504769HCID 178504769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-2-(3-methylsulfanyl-phenoxy)-nicotinamide (70 mg, 0.18 mmol) in tetrahydrofuran (1 ml) was added to a solution of oxone™ (229 mg, 0.37 mmol) in water (1 ml) and isopropylalcohol (4 ml) under nitrogen at room temperature and the reaction was stirred for 3 h. The reaction mixture was passed through a chemelute cartridge, washing with tetrahydrofuran, and the eluent was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (98:2:0.2 changing to 96:4:0.4, by volume) to give 5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-2-(3-methylsulfonyl-phenoxy)-nicotinamide (50 mg) as a yellow solid.

Workup

  1. washwashing with tetrahydrofuran
  2. concentrationthe eluent was concentrated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-cf72b71da5c7455e9de9538d589524f5
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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