HCID 136375592, compound → HCID 135610111, compound

HRID 733375Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:32])=[C:8]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([O:22]CC)=[O:21])(=[O:12])=[O:11])[CH:9]=1)(=[NH:3])[NH2:2]>Cl.C(#N)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:32])=[C:8]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:30])[CH3:31])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:11])=[O:12])[CH:9]=1)(=[NH:2])[NH2:3]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl [2-[2-(5-carbamimidoyl-2-hydroxybenzene-sulfonylamino)ethyl]-5-isopropylphenoxy]acetate (50 mg) was dissolved in a mixture of 3 mL of 1 mol/L hydrochloric acid and 1 mL of acetonitrile at 60° C. The solution was stirred at 60° C. for 4 hours, and the colorless solid obtained by concentration under reduced pressure of the reaction mixture was dissolved in a mixture of 3 mL of 1 mol/L hydrochloric acid and 1 mL of acetnitrile at 60° C. After the solution was stirred at 60° C. for 4 hours, then at room temperature for 10 hours, the reaction mixture was concentrated under reduced pressure to give a colorless solid. The solid was triturated with water and diethyl ether, and collected by filtration to give 31 mg of [2-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)-ethyl]-5-isopropylphenoxy]acetic acid.

Workup

customthe colorless solid obtained by concentration under reduced pressure of the reaction mixture
stirringAfter the solution was stirred at 60° C. for 4 hours
waitat room temperature for 10 hours
concentrationthe reaction mixture was concentrated under reduced pressure
customto give a colorless solid
customThe solid was triturated with water and diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-ba405fda180c419e9697ec6a89cd12fe
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589126B2

Reaction notes

Loading…