Hydrochloric Acid → HCID 136395961, compound

HRID 2295094Notes

Reaction equation

HRID 2295094 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 6M hydrochloric acid (0.7 mL). After refluxing for 19 hours, cyanamide (0.60 g, 14 mmol) and 6M 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-difluoropyridin-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-d29def9c043f4f6da62998a697882f28
Source dataset
uspto-grants-1997_11
Patent number
US05691364

Reaction notes

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