Triethylamine → HCID 68993440, compound

HRID 2196596Notes

Reaction equation

HRID 2196596 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[CH2:16][NH3+:17].[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([CH:28]=[CH2:29])[CH:20]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:17][CH2:16][C:7]2[C:6]3[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:4]([O:3][CH3:2])[CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[O:24])=[C:21]([CH:28]=[CH2:29])[CH:20]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 19809709HCID 19809709, compoundHCID 86621207HCID 86621207, compound

Product 1

HCID 68993440HCID 68993440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6,7-Dimethoxyquinolin-4-yl)methanaminium chloride (0.80 g, 2.8 mmol), 4-chloro-2-vinylbenzoic acid (0.46 g, 2.5 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.58 g, 3.0 mmol) and 1-hydroxybenzotriazole hydrate (0.41 g, 3.0 mmol) were combined in methylene chloride (30 ml), then triethylamine (1.4 ml, 10.0 mmol) was added. The reaction mixture was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (ethyl acetate) to give 4-chloro-N-((6,7-dimethoxyquinolin-4-yl)methyl)-2-vinylbenzamide. MS (ESI, pos. ion) m/z: 383 (M+1).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-85bc251715cd4488afae1627ab6de470
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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