Isopropanol → HCID 178504602, compound

HRID 724343Notes

Reaction equation

HRID 724343 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[N:13][C:12]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=2)[CH2:5][CH2:4]1.C([OH:31])(C)C>O1CCCC1.O.OOS([O-])=O.[K+]>[F:17][C:15]1[CH:14]=[N:13][C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:26])=[O:31])[CH:20]=2)=[C:11]([CH:16]=1)[C:10]([NH:9][C@H:6]1[CH2:7][CH2:8][C@@H:3]([CH2:2][OH:1])[CH2:4][CH2:5]1)=[O:27]

Participants

6

Reactant 2

HCID 3776IsopropanolHCID 178503202HCID 178503202, compound

Product 1

HCID 178504602HCID 178504602, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 23707502Potassium hydroxy sulfiteSolvent

Procedure

N-(cis-4-Hydroxymethyl-cyclohexyl)-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide (120 mg, 0.307 mmol) was dissolved in a solvent mixture of isopropyl alcohol (4 ml), tetrahydrofuran (1 ml) and water (0.5 ml) and oxone™ (132 mg, 0.215 mmol) was added. The reaction was stirred at room temperature for 2 h. The reaction mixture was diluted with water (5 ml) and extracted with dichloromethane (3×10 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2 increasing to 97:3, by volume). The resulting foam was triturated with diethylether (5 ml) to give the product (108 mg) as a white solid.

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane (3×10 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2 increasing to 97:3, by volume)
  6. customThe resulting foam was triturated with diethylether (5 ml)

Sources & evidence

ORD record
ord-2e69842ec1aa4df8a6fe5bfd86a5fd7e
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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