Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 57742965, compound

HRID 1801978Notes

Reaction equation

HRID 1801978 reaction equation
C([O:9][C:10]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([I:20])[CH:18]=2)[N:13]([CH3:21])[C:12](=[O:22])[CH:11]=1)(=O)CCC(OC)=O.Cl[C:24](=[O:31])[CH2:25][CH2:26][C:27]([O:29]C)=[O:28].OC1C2C(=NC=C(I)C=2)N(C)C(=O)C=1>ClCCCl>[OH:9][C:10]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([I:20])[CH:18]=2)[N:13]([CH3:21])[C:12](=[O:22])[C:11]=1[C:24](=[O:31])[CH2:25][CH2:26][C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 67407443HCID 67407443, compoundHCID 67408381HCID 67408381, compound

Product 1

HCID 57742965HCID 57742965, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl methyl succinate. Methyl 4-chloro-4-oxobutyrate (0.08 mL, 0.662 mmol) was added to a suspension of 4-hydroxy-6-iodo-1-methyl-1,8-naphthyridin-2(1H)-one (0.20 g, 0.66 mmol), TEA (0.092 mL, 0.66 mmol) in 1,2-dichloroethane (3 mL). The mixture was stirred for 15 minutes and evaporated. The remaining solids were purified by flash chromatography using EtOAc/hexane to afford the title compound in 60% yield. 1H-NMR (300 MHz, CDCl3) δ ppm 8.78 (1H, d, J=2.2 Hz), 8.34 (1H, d, J=2.2 Hz), 6.68 (1H, s), 3.78 (3H, s), 3.77 (3H, s), 3.02-2.98 (2H, m), 2.84-2.79 (2H, m). MS m/z: 417 (M+).

Workup

  1. customevaporated
  2. customThe remaining solids were purified by flash chromatography

Sources & evidence

ORD record
ord-5ee8efbcdd3940eea02358dd17a9f5ab
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

Loading…