Water → N-(3,5-dichloropyrid-4-yl)-3-(2-fluorocyclopentyloxy)-4-methoxybenzamide

HRID 356908Notes

Reaction equation

HRID 356908 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].[F:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:22](Cl)=[O:23].O>CN(C)C=O>[Cl:11][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[NH:3][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:19]([O:18][CH:14]2[CH2:15][CH2:16][CH2:17][CH:13]2[F:12])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 211878913-(2-Fluorocyclopentyloxy)-4-methoxybenzoyl chloride

Product 1

HCID 21187915N-(3,5-dichloropyrid-4-yl)-3-(2-fluorocyclopentyloxy)-4-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (0.3; 60% oil dispersion) in dimethylformamide (5 mL) is treated with 4-amino-3,5-dichloropyridine (0.62 g) and the mixture is stirred for 40 minutes. A solution of 3-(2-fluoro-cyclopentyloxy)-4-methoxybenzoyl chloride in dimethylformamide (12 mL) is added, and the mixture is stirred at 80°-90° C. for 1 day. The solution is cooled, poured into water (75 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts are washed with brine (50 mL), dried over magnesium sulfate and concentrated. The residue is subjected to flash chromatography, eluting with a mixture of ethyl acetate and petroleum ether (1:3 v/v), to give N-(3,5-dichloropyrid-4-yl)-3-(2-fluorocyclopentyloxy)-4-methoxybenzamide (0.26 g), m.p. 167°-169° C. [Elemental analysis: C,53.8; H,4.2; N,6.75; Cl17.8%; calculated: C,54.15; H,4.3; N,7.0; Cl,17.8%].

Workup

  1. stirringthe mixture is stirred at 80°-90° C. for 1 day
  2. temperatureThe solution is cooled
  3. extractionextracted with dichloromethane (3×50 mL)
  4. washThe combined organic extracts are washed with brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washeluting with a mixture of ethyl acetate and petroleum ether (1:3 v/v)

Sources & evidence

ORD record
ord-8204ee3d397f4a4fa9b10883f862df4c
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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