tert-Butanol → (6-Methoxy-[1,5]naphthyridine-3-yl)-carbamic acid tert-butyl ester

HRID 2279290Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7](C(O)=O)=[CH:6]2.C([N:18]([CH2:21]C)CC)C.[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1>CN(C)C=O>[C:23]([O:27][C:21](=[O:35])[NH:18][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[N:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-methoxy-[1,5]naphthyridine-3-carboxylic acid (24.5 g, 120 mmol, 1.0 eq), triethylamine (50.2 mL, 360 mmol, 3.0 eq) and tert-butanol (292 mL, 3.54 mol, 32 eq) in dimethylformamide (338 mL) is added dropwise to diphenyl phosphoryl azide (49.5 g, 180 mmol. 1.5 eq) to form a yellow clear solution. The mixture is stirred at 70° C. for 40 minutes then warmed to 100° C. for 3 hours. The mixture is cooled to room temperature and concentrated to dryness. The residue is purified by column chromatography (silica gel, eluent: dichloromethane:petroleum ether:ethyl acetate, 25:25:2, v/v/v) to afford (6-methoxy-[1,5]naphthyridine-3-yl)-carbamic acid tert-butyl ester as a yellow solid (23.15 g, 69% yield).

Workup

customto form a yellow clear solution
temperaturethen warmed to 100° C. for 3 hours
temperatureThe mixture is cooled to room temperature
concentrationconcentrated to dryness
customThe residue is purified by column chromatography (silica gel, eluent: dichloromethane:petroleum ether:ethyl acetate, 25:25:2, v/v/v)

Sources & evidence

ORD record: ord-f40321ac24e0420d85c749b845ad2daf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133219B2

Reaction notes

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