Formaldehyde → HCID 86681909, compound

HRID 1749705Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[CH3:22][N:23]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][NH:39][CH3:40])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[CH2:41]=O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:40][N:39]([CH3:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][N:23]([CH3:22])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.050 g, 0.18 mmol) obtained in Example A1, Step 1 in ethanol (3.0 mL) was added with tert-butyl methyl[8-(methylamino)octyl]carbamate (0.074 g, 0.27 mmol), and 37% aqueous formaldehyde (0.017 g, 0.22 mmol), and the mixture was stirred overnight at 70° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain tert-butyl (Z)-8-[({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)(methyl)amino]octyl(methyl)carbamate (0.045 g, 45%).

Workup

customThe solvent was evaporated under reduced pressure
washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record: ord-67f852e158484ded8a0227e97b4192b8
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

Loading…