Triethylamine → HCID 86683405, compound

HRID 579430Notes

Reaction equation

HRID 579430 reaction equation
[I-].[CH:2]([C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]([C:16]([N:18]1[CH:22]=[CH:21][N+:20]([CH3:23])=[CH:19]1)=[O:17])[CH2:9]2)=[O:3].N1(CCN)C[CH2:28][O:27][CH2:26]C1.C(N(CC)CC)C>ClCCl>[N:20]1([CH2:21][CH2:22][NH:18][C:16]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:4]=3[CH:2]=[O:3])[CH2:9]2)=[O:17])[CH2:23][CH2:28][O:27][CH2:26][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 86683403HCID 86683403, compound

Product 1

HCID 86683405HCID 86683405, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-formyl-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-1-methyl-3H-imidazol-1-ium iodide (321 mg, 0.75 mmol), 2-(morpholin-4-yl)-ethylamine (99.5 μL, 99.5 mg, 0.75 mmol) and triethylamine (106 μL, 76 mg, 0.75 mmol) in anhydrous dichloromethane (10 mL) was stirred at room temperature for 24 h. After dilution with dichloromethane (1.0 mL), the solution was washed with brine (2×5 mL), dried over MgSO4 and concentrated. The residue was purified by column chromatography over silica, eluting with a 9:1 mixture of chloroform and methanol. In this manner the title compound (154 mg, 0.44 mmol, 58.7%) was obtained.

Workup

  1. washAfter dilution with dichloromethane (1.0 mL), the solution was washed with brine (2×5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography over silica
  5. washeluting with a 9:1 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-237b382b14ee425fbbe71acfc4154790
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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