Hydrochloric Acid → 3-Fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinic acid

HRID 1685348Notes

Reaction equation

[F:1][C:2]1[C:3]([C:24]([O:26]C)=[O:25])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH3:23])=[CH:17][N:16]=2)=[N:11][CH:10]=1.[OH-].[Na+].O.Cl>C1COCC1>[F:1][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH3:23])=[CH:17][N:16]=2)=[N:11][CH:10]=1

Participants

Conditions

Temperature: 23 °C

Procedure

Methyl 3-fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate (0.061 g, 0.150 mmol) was dissolved in THF (5 mL) and treated aq. NaOH (5N, 0.195 mL, 0.975 mmol). The reaction was stirred at 23° C. for 30 minutes, then water (1 mL) was added and the reaction was stirred for 30 more minutes. The reaction was then acidified with conc. HCl to pH ˜2 and water was added again. This was extracted with ethyl acetate/THF and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (0.035 g, 59%) as a solid which was used as such for the next reaction. HPLC ret. time (Condition B): 1.120 min. LC/MS (M+H)+: 393.

Workup

stirringthe reaction was stirred for 30 more minutes
additionwas added again
extractionThis was extracted with ethyl acetate/THF
dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4d5f9b8345974b368add3ec739868c38
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148400B2

Reaction notes

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