Tetrahydrofuran → {4-[3-(1-Aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]-1H-pyrazol-1-yl}acetonitrile

HRID 510907Notes

Reaction equation

HRID 510907 reaction equation
[C:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][C:18]#[N:19])[CH:16]=2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+].O1CCCC1>CO.C(#N)C>[NH2:28][CH:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][C:18]#[N:19])[CH:16]=2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86666824[4-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)-1H-pyrazol-1-yl]acetonitrile

Product 1

HCID 86666825{4-[3-(1-Aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]-1H-pyrazol-1-yl}acetonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of [4-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)-1H-pyrazol-1-yl]acetonitrile (0.10 g, 0.33 mmol), ammonium acetate (0.254 g, 3.29 mmol) and 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.82 mL, 0.82 mmol) in methanol (0.9 mL) and acetonitrile (0.9 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 C15H15ClN3O (M−NH2)+: m/z=288.1. found: 288.0.

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-872fd09985244437ac1551040e5112b5
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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