Monomethyl terephthalate → HCID 69157125, compound

HRID 750304Notes

Reaction equation

HRID 750304 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].[CH3:31][O:32][C:33](=[O:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:38](=[O:39])[C:37]3[CH:36]=[CH:35][C:34]([C:33]([O:32][CH3:31])=[O:43])=[CH:42][CH:41]=3)=[CH:28][CH:29]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

7

Reactant 4

HCID 15513Monomethyl terephthalateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 44451607HCID 44451607, compound

Product 1

HCID 69157125HCID 69157125, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-aminobenzyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (139 mg) in dichloromethane (5 ml) were added terephthalic acid monomethyl ester (65 mg), 1-hydroxy-1H-benzotriazole (64 mg) and dimethylpyridin-4-yl-amine (51 mg), and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (103 mg) was added at room temperature. The mixture was stirred at room temperature for 15 hrs. Dichloromethane was added, and the mixture was washed with 1N hydrochloric acid and saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0-+9/1) to give the title compound (103 mg, 55%).

Workup

  1. washthe mixture was washed with 1N hydrochloric acid and saturated brine
  2. customdried
  3. additionby adding sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0-+9/1

Sources & evidence

ORD record
ord-2df21b3a05a74421a098e1ba0dd50264
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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