Hydrochloric Acid → Ethyl benzoate

HRID 991483Notes

Reaction equation

HRID 991483 reaction equation
NC1C=C(C=CC=1)OC1C(F)=C(O[C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=2OC)C(F)=C(OC2C=C(C#N)C=C(OC)C=2C2C=CC=CC=2)N=1.N#CN.Cl>C(O)C>[C:18]([O:20][CH2:21][CH3:22])(=[O:19])[C:17]1[CH:23]=[CH:24][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9864Cyanamide2×HCID 86584669HCID 86584669, compound

Product 1

HCID 7165Ethyl benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (15 mL) was added 4-[[2-(3-aminophenoxy)-6-(5-cyano-2-phenyl-methoxyphenoxy)-3,5-difluoropyridin-4-yl]oxy]-3-methoxybenzoic acid, ethyl ester (0.50 g, 0.80 mmol), cyanamide (0.60 g, 14 mmol), and 6 M hydrochloric acid (0.7 mL). After refluxing for 19 hours, cyanamide (0.60 g, 14 mmol) and 6 M hydrochloric acid (0.7 mL) was added and refluxing was continued for 4 hours. The reaction mixture was concentrated in vacuo and purified by HPLC to give 4-[[2-[3-(guanidino)phenoxy)-6-(5-cyano-2-benzyloxyphenoxy)-3,5-difluoro-pyridin-4-yl)oxy]-3-methoxy]benzoic acid, ethyl ester.

Workup

  1. temperatureAfter refluxing for 19 hours
  2. temperaturerefluxing
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-a0453c1b7fa0487a825f3ef8910a114d
Source dataset
uspto-grants-2002_10
Patent number
US06465459B2

Reaction notes

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