Water → HCID 58746193, compound

HRID 724341Notes

Reaction equation

HRID 724341 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[F:7][C:8]1[CH:9]=[N:10][C:11]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27](SC)[CH:26]=2)=[C:12]([CH:23]=1)[C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22])=[O:14].O.[CH:34](O)(C)C>>[F:7][C:8]1[CH:9]=[N:10][C:11]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([S:3]([CH3:34])(=[O:5])=[O:2])[CH:30]=2)=[C:12]([CH:23]=1)[C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22])=[O:14]

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 23707502Potassium hydroxy sulfiteHCID 58746209HCID 58746209, compound

Product 1

HCID 58746193HCID 58746193, compound

Procedure

Oxone™ (245 mg, 0.40 mmol) was added to a solution of 5-fluoro-N-[(1S,2R)-2-hydroxycyclohexyl]-2-[3-(methylsulfanyl)phenoxy]nicotinamide (50 mg, 0.13 mmol) in a mixture of isopropanol (2 ml), tetrahydrofurann (1 ml) and water (1 ml) at 0° C. The mixture was warmed to ambient temperature and stirred for 18 h then partitioned between water (2 ml) and dichloromethane (10 ml) using a Chemelute™ cartridge. The organic phase was evaporated and the residue purified by flash column chromatography using dichloromethane:methanol (98:2) as eluant to give 5-fluoro-N-[(1S,2R)-2-hydroxycyclohexyl]-2-[3-(methylsulfonyl)phenoxy]nicotinamide (39 mg) as a colourless glass.

Workup

  1. customthen partitioned between water (2 ml) and dichloromethane (10 ml)
  2. customThe organic phase was evaporated
  3. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-ba1e40c19cb34d5bbba2a80af08b9230
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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