Hydrochloric Acid → HCID 11306854, compound

HRID 2054589Notes

Reaction equation

HRID 2054589 reaction equation
C([O:3][C:4](=[O:41])[C:5]([NH:7][C:8]1[C:9](=[O:40])[N:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:13]=1)=[O:6])C.[OH-].[Na+].Cl>O1CCOCC1>[CH2:33]([N:10]1[CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]([OH:41])=[O:3])[C:9]1=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59655985HCID 59655985, compound

Product 1

HCID 11306854HCID 11306854, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-oxalamic acid ethyl ester (110 mg, 0.203 mmol) in 1,4-dioxane (4 mL) was treated with NaOH (24 mg, 3 equiv., 0.6 mmol) and stirred at room temperature. After 4 h, the solution was acidified with 10% HCl to pH<5. The resulting precipitate was filtered and washed with ether (2×2 mL) to give N-[1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-oxalamic acid as a white solid (102.4 mg, 99%). Mp 220-223° C.; Rf 0.63 (50% methanol in ethyl acetate), 1H NMR (DMSO-d6, 300 MHz) δ 10.36 (s, 1H), 8.74 (d, J=2.4 Hz, 1H), 8.20-7.99 (m, 5H), 7.72, (dd, J1=10.2 Hz, J2=8.1 Hz, 4H), 7.53-7.28 (m, 7H), 5.28 (s, 2H) ); ESI-LCMS m/z calcd for C32H22N2O5: 514; found 515 (M+1)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ether (2×2 mL)

Sources & evidence

ORD record
ord-a2c90afa39bf49c3b4bd8852e8f5d747
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

Loading…