Dimethylacetamide → HCID 178492486, compound

HRID 218842Notes

Reaction equation

HRID 218842 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.Cl.Cl.[NH2:33][CH2:34][CH2:35][NH:36][C:37]([NH2:39])=[NH:38].CC(N(C)C)=O.C(N(CC)C(C)C)(C)C>>[OH:25][C:24]1[C:4]2[O:3][C:2]([NH:33][CH2:34][CH2:35][NH:36][C:37]([NH2:39])=[NH:38])=[C:6]([C:7](=[O:20])[C:8]3[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=3)[C:5]=2[CH:21]=[CH:22][C:23]=1[O:29][CH3:30]

Participants

5

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuranHCID 178478821HCID 178478821, compound

Product 1

HCID 178492486HCID 178492486, compoundYield 28.5%

Procedure

To a mixture of 0.02 g (0.046 mmol) of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran and 0.02 g (0.11 mmol) of N-(2-aminoethyl)guanidine dihydrochloride (prepared by Fontand & Pignatti, J. Label. Compd. Radiopharm., 2002, 45, 899-909) in 0.5 ml of anhydrous dimethylacetamide 0.032 ml (0.184 mmol) of N,N-diisopropylethylamine was added at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 30 h at room temperature, then evaporated to dryness in vacuo. The residue was purified by flash column chromatography (silica gel, acetonitrile/water 9:1) to give the title compound as a yellowish solid (0.006 g, 28%); 1H NMR (CD3OD) δ 3.55 (tr, 2H, CH2, J=6 Hz); 3.7-3.86 (m, 14H, OMe×4, CH2); 4.82 (s, H2O); 6.32 (d, 1H, CH aromatic, J=8.47 Hz); 6.69 (d, 1H, CH aromatic, J=8.47 Hz); 6.94 (s, 2H, CH aromatic). MS (m/z) 458.9; 459.9, 460.9.

Workup

  1. additionwas added at room temperature under nitrogen atmosphere
  2. customevaporated to dryness in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel, acetonitrile/water 9:1)

Sources & evidence

ORD record
ord-6c9be8c1a1684c8ba191008ffb74cb50
Source dataset
uspto-grants-2012_06
Patent number
US08198466B2

Reaction notes

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