Hydrochloric Acid → [(7-{[(4-Fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]naphthyridin-5-yl)sulfanyl]acetic Acid

HRID 897305Notes

Reaction equation

Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[SH:24][CH2:25][C:26]([OH:28])=[O:27].C(N(CC)CC)C.Cl>COCCOCCOC>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([S:24][CH2:25][C:26]([OH:28])=[O:27])[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-[1,6]naphthyridine-7-carboxamide (0.40 g, 1.05 mmol), mercaptoacetic acid (0.11 mL, 1.60 mmol), triethylamine (0.59 mL, 4.2 mmol) in diglyme (2.5 mL) was heated with stirring at 130° C. under an atmosphere of nitrogen for 18 hours. The product mixture was treated with 1 M aq HCl at 0° C. The resulting yellow solid was filtered, washed with diethyl ether to provide the title acid.

Workup

temperaturewas heated
filtrationThe resulting yellow solid was filtered
washwashed with diethyl ether

Sources & evidence

ORD record: ord-97b8e5b46c914587aeadb78523057474
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921759B2

Reaction notes

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