Ammonium formate → 2-[2-ethyl-3,5-dihydroxy-6-(4-methoxybenzoyl)phenyl]-N-(2-hydroxyethyl)-N-(2-morpholinoethyl)acetamide

HRID 499887Notes

Reaction equation

C([O:4][C:5]1[C:6]([CH2:40][CH3:41])=[C:7]([CH2:25][C:26]([N:28]([CH2:37][CH2:38][OH:39])[CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:27])[C:8]([C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:9]([O:11]CC=C)[CH:10]=1)C=C.C([O-])=O.[NH4+]>O1CCOCC1.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd][P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH2:40]([C:6]1[C:5]([OH:4])=[CH:10][C:9]([OH:11])=[C:8]([C:15](=[O:24])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:7]=1[CH2:25][C:26]([N:28]([CH2:37][CH2:38][OH:39])[CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1)=[O:27])[CH3:41]

Participants

Conditions

Temperature: 100 °C

Procedure

2-[3,5-Diallyloxy-2-ethyl-6-(4-methoxybenzoyl)-phenyl]-N-(2-hydroxyethyl)-N-(2-morpholinoethyl)acetamide (0.31 g, 0.55 mmol) obtained in Example 110, Step 2 was dissolved in 1,4-dioxane (1.5 mL), and ammonium formate (0.14 g, 2.2 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.012 g, 0.017 mmol) were added thereto, followed by stirring at 100° C. for 1.5 hours in an atmosphere of argon. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by C18 silica gel column chromatography (water-water/acetonitrile=1/1) to obtain Compound III (0.14 g, 51%).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by C18 silica gel column chromatography (water-water/acetonitrile=1/1)

Sources & evidence

ORD record: ord-c406834d1bc14f3fa4d1df60f70e1f8e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767693B2

Reaction notes

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