Acetic Acid → Methyl 8-hydroxy-5-[methyl(ethylsulfonyl)amino]-1,6-naphthyridine-7-carboxylate

HRID 2252821Notes

Reaction equation

C[O-].[Na+].[CH3:4][N:5]([S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])[C:6]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([O:20]S(C2C=CC(C)=CC=2)(=O)=O)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.C(O)(=O)C.O>CO.CN(C=O)C>[OH:20][C:13]1[C:14]([C:16]([O:18][CH3:19])=[O:17])=[N:15][C:6]([N:5]([CH3:4])[S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of sodium methoxide (479 mg, 8.86 mmol) in dry methanol (18 mL) was added to methyl 5-[methyl(ethylsulfonyl)amino]-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (1.7 g, 3.54 mmol) dissolved in a minimum amount of DMF and the resulting solution was heated to 50° C. for 5 minutes. The reaction was cooled, glacial acetic acid (0.433 mL, 7 mmol) was added followed by water (0.936 mL) over 15 minutes at 25 degrees C. The resulting solid was collected by filtration and washed with 1:1 water methanol and dried in vacuo to give the desired product as a yellow solid.

Workup

temperatureThe reaction was cooled
filtrationThe resulting solid was collected by filtration
washwashed with 1:1 water methanol
customdried in vacuo

Sources & evidence

ORD record: ord-64372e703aeb488d9b7acdf6811ea0ba
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323460B2

Reaction notes

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