Ethyl Acetate → N-{3-[4-(6-Cyclopropylmethoxypyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide

HRID 1260558Notes

Reaction equation

HRID 1260558 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH:25]1([CH2:28][OH:29])[CH2:27][CH2:26]1.C(OCC)(=O)C>CN1C(=O)CCC1.O>[CH:25]1([CH2:28][O:29][C:2]2[N:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=3)=[CH:4][CH:3]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 67302905N-{3-[4-(6-Fluoropyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide

Product 1

HCID 67303389N-{3-[4-(6-Cyclopropylmethoxypyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-{3-[4-(6-Fluoropyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide (105 mg, 0.35 mmol), sodium hydride (55% in oil) (42 mg, 1.04 mmol) and cyclopropylmethanol (62 mg, 0.86 mmol) were stirred in 3 ml of NMP at 130° C. under argon for 9 h. After cooling, ethyl acetate and water were added, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 71 mg (58%), M+H+: 355.1.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-3562ff433e0e4284a4a9ac3c81c5fe7e
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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