Methanol → HCID 22046385, compound

HRID 1821748Notes

Reaction equation

C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)=[O:12])=[C:6]([O:24][CH3:25])[CH:5]=1.CO.O.[OH-].[Li+]>O>[CH3:25][O:24][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][N:15]=1)=[O:12])[C:3]([OH:26])=[O:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of 3-methoxy-4-[3-(5-trifluoromethyl-pyrazin-2-yl)-ureido]-benzoic acid methyl ester (213 mg, 0.575 mmol) in 5.75 mL 3:1 MeOH:H2O at room temperature under nitrogen was added lithium hydroxide monohydrate (240 mg, 5.8 mmol) and the reaction warmed to 65° C. After reaching temperature, the suspension gradually became a bright yellow solution. After about 4 hours a precipitate formed but the reaction was continued overnight. After cooling to RT, MeOH was removed by rotovap and the aqueous suspension neutralized to pH=5 with concentrated HCl; As pH=5 was approached, the suspension turned from yellow to white. The suspension was then filtered through paper on a ceramic funnel. When most of the H2O was removed the residue was dryed under high vacuum in a dessicator overnight (133 mg, 55%).

Workup

customAfter about 4 hours a precipitate formed
temperatureAfter cooling to RT
customMeOH was removed by rotovap
filtrationThe suspension was then filtered through paper on a ceramic funnel
customWhen most of the H2O was removed the residue
customwas dryed under high vacuum in a dessicator overnight (133 mg, 55%)

Sources & evidence

ORD record: ord-91ec2851ac404d57875838931d413f98
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608618B2

Reaction notes

Loading…