Hydrochloric Acid → HCID 136395961, compound

HRID 381463Notes

Reaction equation

HRID 381463 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[O:5][C:6]1[C:11]([F:12])=[C:10]([O:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=2[O:25][CH3:26])[C:9]([F:27])=[C:8]([O:28][C:29]2[CH:34]=[C:33]([C:35]#[N:36])[CH:32]=[CH:31][C:30]=2[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:7]=1.[N:48]#[C:49][NH2:50].Cl>C(O)C>[NH:1]([C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[O:5][C:6]1[C:11]([F:12])=[C:10]([O:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=2[O:25][CH3:26])[C:9]([F:27])=[C:8]([O:28][C:29]2[CH:34]=[C:33]([C:35]#[N:36])[CH:32]=[CH:31][C:30]=2[O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:7]=1)[C:49]([NH2:50])=[NH:48]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9864Cyanamide2×HCID 86751676HCID 86751676, compound

Product 1

HCID 136395961HCID 136395961, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (15 mL) was added 4-[[2-(3-aminophenoxy)-6-(5-cyano-2-phenylmethoxyphenoxy)-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 9, 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-methoxybenzoic 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-7b017b0019dd46f491b8ddfa4947b878
Source dataset
uspto-grants-2001_10
Patent number
US06306884B1

Reaction notes

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