1,4-Dioxane → HCID 22051042, compound

HRID 1867131Notes

Reaction equation

HRID 1867131 reaction equation
C([C:5]1([NH:31]C(=O)[O-])[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])=[C:14]([Br:29])[C:13]2=[O:30])=[CH:7][CH2:6]1)(C)(C)C.O1CCOCC1>Cl.C(OCC)C>[NH2:31][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]2[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])=[C:14]([Br:29])[C:13]2=[O:30])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 86591588HCID 86591588, compound

Product 1

HCID 22051042HCID 22051042, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

1-tert-butyl-4-{[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]methyl}phenylcarbamate (Step 1) (6.14 g, 11.47 mmol) was suspended in 4N HCl in dioxane (5.74 mL, 22.94 mmol). The reaction mixture was stirred at room temperature for 1 hour then diluted with diethyl ether. The precipitate was collected by filtration and washed with diethyl ether (3×30 mL) to afford a tan solid (3.45 g, 69%). 1H NMR (400 MHz, DMF-d6) δ 7.64 (app dt, J=6.58, 8.59 Hz, 1H), 7.31 (ddd, J=2.55, 9.53, 10.61 Hz, 1H) 7.29-7.12 (m, 5H), 6.56 (s, 1H), 5.28 (s, 2H), 5.27 (s, 2H), 2.28 (s, 3H). ES-HRMS m/z 435.0516 (M+H calcd for C20H18BrF2N2O2 requires 435.0514).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with diethyl ether (3×30 mL)

Sources & evidence

ORD record
ord-e9b6bf4a4d5f47b3ac27a2b10cb562af
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…