1-Hydroxybenzotriazole → Methyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate

HRID 1042333Notes

Reaction equation

HRID 1042333 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([OH:26])=[O:25])=[CH:5][CH:4]=1.[CH:27]1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 42596938Clt-28643

Product 1

HCID 58173127Methyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 0.1 g of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3-carboxylic acid in dichloromethane EDC.HCl (1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride, 0.161 g), HOBt (N-hydroxybenzotriazole, 0.042 g), DMAP (4-dimethylaminopyridine, 0.17 g) and 20 mL of methanol were added and the reaction mixture was stirred at room temperature for 3 h. After aqueous work up, the reaction mixture was extracted, concentrated and dried over anhydrous sodium sulfate to afford the crude product which was later purified by column chromatography to afford 0.062 g (60%) of methyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 11.51 (s, 1H, —NH—), 9.12 (s, 1H, aromatic), 8.38-8.15 (m, 2H, aromatic), 8.10 (s, 1H, aromatic), 7.23 (d, 2H, J=9 Hz, aromatic), 7.02 (d, 2H, J=9 Hz, aromatic), 4.02 (s, 3H, —OCH3), 3.90 (s, 3H, —OCH3), 2.92 (s, 3H, —NCH3); LC-MS (m/z) 365.9 (M+1).

Workup

  1. additionwere added
  2. extractionAfter aqueous work up, the reaction mixture was extracted
  3. concentrationconcentrated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto afford the crude product which
  6. customwas later purified by column chromatography

Sources & evidence

ORD record
ord-16c0d327600543d1b9121fe00b72733a
Source dataset
uspto-grants-2013_10
Patent number
US08557843B2

Reaction notes

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