HCID 67083028, compound → HCID 67083031, compound

HRID 2368683Notes

Reaction equation

HRID 2368683 reaction equation
O[C:2]([C:14]1[C:15]([NH:20][C:21](=[O:26])[C:22](C)(C)C)=[N:16][CH:17]=[CH:18][CH:19]=1)([CH:11]([CH3:13])[CH3:12])CC(OC(C)(C)C)=O>Cl>[CH:11]([C:2]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[NH:20][C:21](=[O:26])[CH:22]=1)([CH3:12])[CH3:13]

Participants

3

Reactant 1

HCID 67083028HCID 67083028, compound

Product 1

HCID 67083031HCID 67083031, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 3-hydroxy-4-methyl-3-(2-pivalamidopyridin-3-yl)pentanoate (3.78 g, 10.4 mmol) in 12.0 mL 3N HCl were reacted as outlined in Scheme 1 to give the desired 4-isopropyl-1,8-naphthyridin-2(1 H)-one (800 mg, 41%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.34 (d, J=7.03 Hz, 6 H) 3.34 (quin, J=6.81 Hz, 1 H) 6.66 (s, 1 H) 7.23 (dd, J=12.31, 4.10 Hz, 2 H) 8.09 (dd, J=8.06, 1.61 Hz, 1 H) 8.71 (dd, J=4.69, 1.47 Hz, 1 H) 11.98 (br. s., 1 H).

Sources & evidence

ORD record
ord-938263de96f245e0af03f039db65c249
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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