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

HRID 1042332Notes

Reaction equation

HRID 1042332 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]1[CH:28]=CC2N(O)N=N[C:31]=2[CH:32]=1>CN(C1C=CN=CC=1)C.C(O)CCC>[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][CH2:28][CH2:27][CH2:32][CH3:31])=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 42596938Clt-28643

Product 1

HCID 58173126Butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylateYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 2631-ButanolSolvent

Procedure

To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3-carboxylic acid (0.1 g) 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 n-butanol (25 mL) were added, and the reaction mixture was stirred at room temperature for 3 hours. After aqueous work up, the reaction mixture was extracted, concentrated and dried over anhydrous sodium sulphate to afford the crude product which was later purified by column chromatography to afford 0.05 g (55% yield) of butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 10.84 (s, 1H, —NH—), 9.21 (s, 1H, aromatic), 8.05 (d, 1H, J=8.8 Hz, aromatic), 7.97 (d, 1H, J=8.8 Hz, aromatic), 7.80 (s, 1H, aromatic), 7.16 (d, 2H, J=8.7 Hz, aromatic), 6.96 (d, 2H, J=8.7 Hz, aromatic), 5.60 (s, 1H, —NHCH3—), 4.41 (t, 2H, J=6.6 Hz, —O—CH2—), 3.87 (s, 3H, —OCH3), 2.88 (s, 3H, —NCH3), 1.92-1.75 (m, 2H, —O—CH2—CH2—CH2—), 1.65-1.46 (m, 2H, —O—CH2—CH2—CH2—), 1.12-0.98 (m, 3H, —CH3); LC-MS (m/z) 407.9 (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 sulphate
  5. customto afford the crude product which
  6. customwas later purified by column chromatography

Sources & evidence

ORD record
ord-933f88ed50dd4a50940387e302d64593
Source dataset
uspto-grants-2013_10
Patent number
US08557843B2

Reaction notes

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