Tetrahydrofuran → 1-[6-(1-Aminoethyl)-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-yl]pyrrolidin-2-one

HRID 510839Notes

Reaction equation

HRID 510839 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[C:8]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[C:7]([CH3:24])=[C:6]([Cl:25])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+].O1CCCC1>CO.C(#N)C>[NH2:32][CH:1]([C:4]1[C:9]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[C:8]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[C:7]([CH3:24])=[C:6]([Cl:25])[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 866667701-(6-Acetyl-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-yl)pyrrolidin-2-one

Product 1

HCID 866667711-[6-(1-Aminoethyl)-4-chloro-3',5'-difluoro-3-methylbiphenyl-2-yl]pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(6-acetyl-4-chloro-3′,5′-difluoro-3-methylbiphenyl-2-yl)pyrrolidin-2-one (0.015 g, 0.041 mmol), ammonium acetate (0.032 g, 0.41 mmol), 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.10 mL, 0.10 mmol) in methanol (0.1 mL) and acetonitrile (0.1 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 and concentrated to give the desired product. LCMS calculated for C19H17ClF2NO (M−NH2)+: m/z=348.1. found: 348.0.

Workup

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

Sources & evidence

ORD record
ord-62e1a2ae3181474a968cb7a20c01513d
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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