2-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine → HCID 178479190, compound

HRID 1654861Notes

Reaction equation

HRID 1654861 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[NH:14])OCC.[NH2:15][C:16]1[C:21]([O:22][CH2:23][C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:31])=[CH:20][CH:19]=[CH:18][N:17]=1>C(O)C>[ClH:2].[Cl:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=1[CH2:23][O:22][C:21]1[C:16]([NH:15][C:10](=[NH:14])[CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridineHCID 12283339HCID 12283339, compound

Product 1

HCID 178479190HCID 178479190, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-chlorophenylacetimidate hydrochloride (5.07 g, 0.0216 mol), 2-amino-3-(2-chloro-6-fluorobenzyloxy)pyridine (4.95 g, 0.0196 mol)and ethanol (150 ml) was heated under reflux for 2 hours. The solvent was evaporated off and the resultant oil was purified by chromatography (silica gel, 1% methanol/dichloromethane) and trituration with ether. Yield 0.7 g (8%), m.p. 156°-158 ° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was evaporated off
  4. customthe resultant oil was purified by chromatography (silica gel, 1% methanol/dichloromethane) and trituration with ether

Sources & evidence

ORD record
ord-a22a4c767e824042b67a6522426f9f56
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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