Tetrahydrofuran → 1-[5-Chloro-2-methoxy-4-methyl-3-(1,3-thiazol-4-yl)phenyl]ethanamine

HRID 510926Notes

Reaction equation

HRID 510926 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([C:13]2[N:14]=[CH:15][S:16][CH:17]=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:25].[Na+].C1COCC1>CO.C(#N)C>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:25])[CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 866668401-[5-Chloro-2-methoxy-4-methyl-3-(1,3-thiazol-4-yl)phenyl]ethanone

Product 1

HCID 866668411-[5-Chloro-2-methoxy-4-methyl-3-(1,3-thiazol-4-yl)phenyl]ethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[5-chloro-2-methoxy-4-methyl-3-(1,3-thiazol-4-yl)phenyl]ethanone (6.0 mg, 0.021 mmol), ammonium acetate (20 mg, 0.2 mmol) and 1.0 M sodium cyanoborohydride in THF (0.053 mL, 0.053 mmol) in methanol (0.05 mL)/acetonitrile (0.05 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the crude product, which was used in the next step directly. LCMS calculated for C13H13ClNOS (M−NH2)+: m/z=266.1. found: 266.0.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with sat. NaHCO3 solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56a8bffc782a47caabc4d4355bee61f6
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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