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

HRID 495199Notes

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 111 (0.14 g, 51%). Melting Point: 235-237° C.

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-3220960cd6cd45c9a01a3b0dee44abf1
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538224B2

Reaction notes

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