Trifluoroacetic acid → HCID 67288576, compound

HRID 1191998Notes

Reaction equation

HRID 1191998 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[O:6][C:7]2[C:27]([OH:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][C:8]=2[C:9]=1[C:10]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[O:11].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[O:6][C:7]2[C:27]([OH:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][C:8]=2[C:9]=1[C:10]([C:12]1[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)=[O:11]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24880184HCID 24880184, compound

Product 1

HCID 67288576HCID 67288576, compoundYield 42%

Procedure

0.026 g (0.05 mmol) of [2-(2-aminoethylamino)-7-hydroxy-6-methoxybenzofuran-3-yl](3,4,5-trimethoxyphenyl)methanone was dissolved in 1 ml of anhydrous trifluoroacetic acid. After stirring for 1 h at room temperature the solvent was removed under reduced pressure and the residue was suspended in 2 ml of anhydrous methylene chloride and evaporated under reduced pressure. The residue was washed with 2 ml of anhydrous methylene chloride to give the title compound as a yellowish solid (0.011 g, 42%); 1H NMR (CD3OD) δ 3.31 (tr, 2H, CH2, J=%0.84 Hz); 3.8 (s, 9H, OMe); 3.83 (s, 3H, OMe); 3.92 (tr, 2H, CH, J=5.84 Hz); 6.33 (d, 1H CH aromatic, J=8.52 Hz); 6.69 (d, 1H, CH aromatic, J=8.52 Hz); 6.95 (s, 2H, CH aromatic).

Workup

  1. customwas removed under reduced pressure
  2. customevaporated under reduced pressure
  3. washThe residue was washed with 2 ml of anhydrous methylene chloride

Sources & evidence

ORD record
ord-63e2bb62a11a4a0091a7739c38e1dd6a
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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