Triethylamine → HCID 22395313, compound

HRID 1071864Notes

Reaction equation

HRID 1071864 reaction equation
[NH:1]=[C:2]1[CH:11]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([C:20]2[CH:25]=[C:24]3[O:26][CH2:27][O:28][C:23]3=[C:22]([O:29][CH3:30])[CH:21]=2)[C:9]2[C:4](=[CH:5][C:6]([N:31]([CH3:33])[CH3:32])=[CH:7][CH:8]=2)[O:3]1.C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:20]3[CH:25]=[C:24]4[O:26][CH2:27][O:28][C:23]4=[C:22]([O:29][CH3:30])[CH:21]=3)[C:11]=1[C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[CH:8][CH:7]=[C:6]([N:31]([CH3:32])[CH3:33])[CH:5]=2

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 22395345HCID 22395345, compound

Product 1

HCID 22395313HCID 22395313, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-imino-3-benzoyl-7-dimethylamino 4-(3-methoxy-4,5-methylenedioxyphenyl)-chromane (26 mg, 0.059 mmol) and triethylamine (0.1 ml) in ethanol (5 ml) was refluxed for 12 h. It was concentrated, and the residue was purified by column chromatography (silica gel, EtOAc/Hexane=1:5) to give 18 mg (72%) of the title compound. 1H NMR (CDCl3): 7.40-7.30 (m, 2H), 7.18-7.14 (m, 2H), 6.86 (d, 1H), 6.50-6.34 (m, 2H), 6.00 (d, 1H), 5.85-5.81 (m, 2H), 5.73 (d, 1H), 4.73 (s, 1H), 3.67 (s, 3H), 2.91 (s, 6H).

Workup

  1. concentrationIt was concentrated
  2. customthe residue was purified by column chromatography (silica gel, EtOAc/Hexane=1:5)

Sources & evidence

ORD record
ord-c97b8e8f99534d54b79559d3d741c3b7
Source dataset
uspto-grants-2005_06
Patent number
US06906203B1

Reaction notes

Loading…