Formic Acid → N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-[2-(N-formylamino)ethoxy]-3-methoxyphenylacetamide

HRID 7076Notes

Reaction equation

[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]3[CH2:36][CH2:35][CH:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:33][CH2:32]3)[CH:26]=2)=[O:23])=[CH:17][C:16]=1[O:41][CH3:42]>O1CCCC1>[C:37]([CH:34]1[CH2:33][CH2:32][CH:31]([C:27]2[CH:26]=[C:25]([NH:24][C:22](=[O:23])[CH2:21][C:18]3[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][NH:11][CH:1]=[O:2])=[C:16]([O:41][CH3:42])[CH:17]=3)[CH:30]=[CH:29][CH:28]=2)[CH2:36][CH2:35]1)([CH3:38])([CH3:39])[CH3:40]

Participants

Conditions

Temperature: 60 °C

Procedure

Formic acid (30 mg) is slowly added to acetic anhydride (75 mg), and the mixture is heated with stirring at 60° C. for 2 hours. To the mixture is added dry tetrahydrofuran (0.2 ml), and further added 4-(2-aminoethoxy)-N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-3-methoxyphenylacetamide (100 mg) obtained in Example 62 at −20° C. The mixture is stirred at room temperature for 3 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (80 mg).

Workup

temperaturethe mixture is heated
stirringThe mixture is stirred at room temperature for 3 hours
customThe solvent is evaporated under reduced pressure
customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7a9766c478ba4aec9949a59023cce479
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084176B2

Reaction notes

Loading…