Tetrahydrofuran → HCID 59846230, compound

HRID 1697092Notes

Reaction equation

HRID 1697092 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([C:15](=[O:28])[CH2:16][CH2:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1.CC1N=C(NC2C=CC=CC=2)C([C:43](=[O:55])[CH2:44]CC2C=NC(S(C)=O)=CC=2)=CC=1.C1C[O:59][CH2:58]C1>C1(C)C=CC=CC=1>[CH3:58][O:59][C:43]([C:44]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[C:5]([C:15](=[O:28])[C:16]=1[CH2:17][C:18]1[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1)=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[O:55]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 66816222HCID 66816222, compoundHCID 66817062HCID 66817062, compound

Product 1

HCID 59846230HCID 59846230, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A 2:1 mixture of 1-(6-methyl-2-phenylamino-pyridin-3-yl)-3-(6-methylsulfonyl-pyridin-3-yl)-propan-1-one and 1-(6-methyl-2-phenylamino-pyridin-3-yl)-3-(6-methylsulfinyl-pyridin-3-yl)-propan-1-one (0.22 g) was dissolved in THF (3 mL) and toluene (1.5 mL), and monomethyl oxalyl chloride (0.27 g) added. The mixture was heated to 80° C. for 2.5 h, concentrated to a semi-solid, taken up in MeOH, and K2CO3 (0.22 g) added. This mixture was heated to 80° C. for 15 min, then cooled to RT. The product was worked up in EtOAc/H2O, the organic layer washed with LiCl (2×, 0.3 wt % aq), dried over MgSO4, and purified by prep TLC (1:1 EtOAc/hexane) to provide 3-(6-methanesulfonyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 92) (8 mg) as a yellow solid. M+H=464, mp=217-218° C.

Workup

  1. concentrationconcentrated to a semi-solid
  2. additionK2CO3 (0.22 g) added
  3. temperatureThis mixture was heated to 80° C. for 15 min
  4. temperaturecooled to RT
  5. washthe organic layer washed with LiCl (2×, 0.3 wt % aq)
  6. dry with materialdried over MgSO4
  7. custompurified by prep TLC (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-88f646db02ee4588bbb621a3caa29896
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

Loading…