Tetrahydrofuran → HCID 86711468, compound

HRID 2274112Notes

Reaction equation

HRID 2274112 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=2)[C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=2)[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:30])[CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86711467HCID 86711467, compound

Product 1

HCID 86711468HCID 86711468, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-{5-chloro-2-methoxy-4-methyl-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethanone (0.035 g, 0.099 mmol), ammonium acetate (0.08 g, 1 mmol) and 1.0 M sodium cyanoborohydride in tetrahydrofuran (THF) (0.25 mL, 0.25 mmol) in methanol (0.2 mL) and acetonitrile (0.2 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature (rt), quenched with sat. NaHCO3 solution, and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product, which was used in the next step directly (0.024 g, 69%). LCMS calculated for C16H17ClNO3S (M−NH2)+: m/z=338.1. found: 338.0.

Workup

  1. customquenched with sat. NaHCO3 solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f086211bf48e4057a25bd942384eb551
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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