Triethylamine → HCID 22395313, compound

HRID 1786525Notes

Reaction equation

HRID 1786525 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-b317cfc19b124188b1c578197f6f698d
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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