Tetrahydrofuran → HCID 86666807, compound

HRID 510888Notes

Reaction equation

HRID 510888 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[C:10]([CH3:15])=[N:11][O:12][C:13]=2[CH3:14])[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:4]([C:23](=O)[CH3:24])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[C:10]([CH3:15])=[N:11][O:12][C:13]=2[CH3:14])[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:4]([CH:23]([NH2:32])[CH3:24])[CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86666808HCID 86666808, compound

Product 1

HCID 86666807HCID 86666807, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[4-chloro-6-(3,5-dimethylisoxazol-4-yl)-3′-fluoro-5-methylbiphenyl-2-yl]ethanone (40 mg, 0.11 mmol), ammonium acetate (86 mg, 1.1 mmol) and 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.28 mL, 0.28 mmol) in methanol (0.6 mL) and acetonitrile (0.6 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to give the desired product (35 mg, 87%). LCMS calculated for C20H21ClFN2O (M+H)+: m/z=359.1. found: 359.1.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e02f98b260dc4296832687bc1392f3ee
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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