Potassium Hydroxide → 6-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid

HRID 1778148Notes

Reaction equation

[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[K+]>CO.O>[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of methyl 6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinate, (1.82 g, 4.85 mmol, 1 eq) in MeOH—H2O (100 mL, 3:1) at RT was added potassium hydroxide (2.72 g, 10 eq) with stirring. The mixture was heated at 65° C. for 2 hours and a brown solution was observed at this time. The reaction mixture was concentrated to remove most of the methanol. The resulting solution was cooled to 0° C. and concentrated HCl was added until the pH was around 3 at which time a white precipitates formed. The solid which had formed was collected by filtration, rinsed with water, and dried to give the title compound as a white solid (1.75 g).

Workup

concentrationThe reaction mixture was concentrated
customto remove most of the methanol
temperatureThe resulting solution was cooled to 0° C.
additionconcentrated HCl was added until the pH was around 3 at which time
customa white precipitates
customformed
customThe solid which had formed
filtrationwas collected by filtration
washrinsed with water
customdried

Sources & evidence

ORD record: ord-7a168fab4f624be18aa9f7da721e2c75
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266869B2

Reaction notes

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