HCID 22277869, compound → HCID 9814575, compound

HRID 1063878Notes

Reaction equation

HRID 1063878 reaction equation
C([O:8][N:9]([CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:15]([Cl:25])[CH:14]=1)[CH:10]=[O:11])C1C=CC=CC=1>CO.[Pd]>[CH2:21]([O:20][C:16]1[C:15]([Cl:25])=[CH:14][C:13]([CH2:12][N:9]([OH:8])[CH:10]=[O:11])=[CH:18][C:17]=1[Cl:19])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 22277869HCID 22277869, compound

Product 1

HCID 9814575HCID 9814575, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the crude N-benzyloxy-N-(4-butoxy-3,5-dichlorobenzyl)formamide in 5 ml of methanol was added 100 mg of 10% palladium on carbon. This was stirred under a hydrogen atmosphere for 50 min. Filtration and removal of volatiles in vacuo then purification by preparative HPLC afforded the title compound (71 mg, 41%) as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 8.36, 8.20* (s, 1H); 7.37*, 7.33 (s, 2H); 4.64, 4.61* (s, 2H); 4.01 (t, j=6.4 Hz, 2H), 1.80 (quint, j=7.6 Hz, 2H), 1.57 (sext, j=7.6 Hz, 2H), 1.00 (t, j=7.2 Hz, 3H). M+1=292.*: minor rotamer

Workup

  1. filtrationFiltration and removal of volatiles in vacuo
  2. custompurification by preparative HPLC

Sources & evidence

ORD record
ord-38f04d020f2a496ba387400477829c63
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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