3-[(4-Fluorophenyl)methoxy]pyridin-2-amine → HCID 178479196, compound

HRID 1654823Notes

Reaction equation

HRID 1654823 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:17].[C:18]1([CH2:24][C:25](=[NH:29])OCC)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C.C(Cl)(Cl)Cl>[ClH:17].[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:7]2[C:2]([NH:1][C:25](=[NH:29])[CH2:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 27283773-[(4-Fluorophenyl)methoxy]pyridin-2-amineHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 178479196HCID 178479196, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-amino-3-(4-fluorobenzyloxy)pyridine (5.42 g, 24.2 mmol) and ethyl phenylacetimidate hydrochloride (6.28 g, 26.7 mmol) in ethanol (80 ml) was heated under reflux for 2 hours. Evaporation of the solvent gave an oil which was taken up in chloroform, filtered to remove an insoluble white solid, and purified by flash chromatography (chloroform/methanol) to obtain the product (0.85 g), m.p. 175°-178° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customEvaporation of the solvent
  4. customgave an oil which
  5. filtrationfiltered
  6. customto remove an insoluble white solid
  7. custompurified by flash chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-c7977923c6b44af29cbbc68722df554b
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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