Tetrahydrofuran → 1-{4-Chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3'-fluoro-5-methylbiphenyl-2-yl}ethanamine

HRID 510890Notes

Reaction equation

HRID 510890 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]([O:16][CH2:17][CH3:18])[CH3:15])[CH:13]=2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[C:4]([C:26](=O)[CH3:27])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:35].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]([O:16][CH2:17][CH3:18])[CH3:15])[CH:13]=2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[C:4]([CH:26]([NH2:35])[CH3:27])[CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 866668101-{4-chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3'-fluoro-5-methylbiphenyl-2-yl}ethanone

Product 1

HCID 866668091-{4-Chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3'-fluoro-5-methylbiphenyl-2-yl}ethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-{4-chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3′-fluoro-5-methylbiphenyl-2-yl}ethanone (37 mg, 0.092 mmol), ammonium acetate (71 mg, 0.92 mmol) and 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.23 mL, 0.23 mmol) in methanol (0.5 mL) and acetonitrile (0.5 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate solution, extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to give the desired product (35 mg). LCMS calculated for C22H26ClFN3O (M+H)+: m/z=402.2. found: 402.2.

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-d088a74e59d14da8a6c23d510400bad1
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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