Diisopropylethylamine → ethyl 6-bromo-4-[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylate

HRID 244595Notes

Reaction equation

HRID 244595 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].Cl.[CH3:19][O:20][C@@H:21]([CH3:24])[CH2:22][NH2:23].C(N(C(C)C)CC)(C)C>C(O)C>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:15]2[NH:23][CH2:22][C@@H:21]([O:20][CH3:19])[CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2764138Ethyl 6-bromo-4-chloroquinoline-3-carboxylateHCID 71607326(S)-2-Methoxypropan-1-amine hydrochloride

Product 1

HCID 68108432ethyl 6-bromo-4-[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Suspend ethyl-6-bromo-4-chloro-quinoline-3-carboxylate (389 g, 1.24 mol) and (2S)-2-methoxypropan-1-amine, hydrochloride (171 g, 1.36 mol, 1.1 eq.) in ethanol (5.84 L). Add diisopropylethylamine (474 mL) and heat the mixture at 50° C. overnight. After 16 hours, cool the reaction to room temperature and concentrate in vacuo. Add methyl tert-butyl ether (2 L) to the residue and stir for 20 min. Filter the precipitate and wash it with methyl tert-butyl ether (2×250 mL). Concentrate the filtrate in vacuo to afford the titled compound in almost quantitative yield. The compound will be used in the next step without further purification. MS (ESI) m/z (M+H)+ 367.0, 369.0.

Workup

  1. temperaturecool
  2. customthe reaction to room temperature
  3. concentrationconcentrate in vacuo
  4. filtrationFilter the precipitate
  5. washwash it with methyl tert-butyl ether (2×250 mL)
  6. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-6d5fa84e05894992a374e5e996b82bd8
Source dataset
uspto-grants-2014_02
Patent number
US08658668B2

Reaction notes

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