Water → Ethyl 6-chloro-4-(propylamino)nicotinate

HRID 2284809Notes

Reaction equation

HRID 2284809 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.C(O[C:17]([C:19]1[C:20](NCCC)=[N:21]C(SC)=NC=1)=O)C.C(N(CC)C(C)C)(C)C.O>C(#N)C.C(N)CC.C(OCC)(=O)C>[Cl:13][C:4]1[CH:3]=[C:2]([NH:21][CH2:20][CH2:19][CH3:17])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylateHCID 105629752-Methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester

Product 1

HCID 90051800Ethyl 6-chloro-4-(propylamino)nicotinate

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 7852PropylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4,6-dichloronicotinate (S13, 1.0 g) synthesized according to the method described in US200549419 A1 and N,N-diisopropylethylamine (2.37 mL) in acetonitrile (10 mL), propylamine (0.90 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 5 hours and 30 minutes. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 90% hexane/10% ethyl acetate) to obtain ethyl 6-chloro-4-(propylamino)nicotinate (S14, 1.1 g).

Workup

  1. additionwas added under ice cooling
  2. stirringstirred at room temperature for 5 hours and 30 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 90% hexane/10% ethyl acetate)

Sources & evidence

ORD record
ord-daf2d79a658845aba3726f6b79d049ab
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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