1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(3-Chloro-pyridin-2-ylsulfanyl)-1-(8-methyl-3,4-dihydro-2H-quinolin-1-yl)-ethanone

HRID 1672406Notes

Reaction equation

HRID 1672406 reaction equation
[Cl:1][C:2]1[C:3]([S:8][CH2:9][C:10]([OH:12])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[NH:22][CH2:21][CH2:20][CH2:19]2.CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([S:8][CH2:9][C:10]([N:22]2[C:23]3[C:18](=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:13])[CH2:19][CH2:20][CH2:21]2)=[O:12])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27741668-Methyl-1,2,3,4-tetrahydroquinolineHCID 24711495(3-Chloro-pyridin-2-ylsulfanyl)-acetic acid

Product 1

HCID 249005712-(3-Chloro-pyridin-2-ylsulfanyl)-1-(8-methyl-3,4-dihydro-2H-quinolin-1-yl)-ethanoneYield 33%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-chloro-pyridin-2-ylsulfanyl)-acetic acid (19, 0.27 g, 1.3 mmol) in 12 mL of dry THF at 0° C. was added neat 8-methyl-1,2,3,4-tetrahydroquinolin (0.20 g, 1.3 mmol) followed by addition of DMAP (0.19 g, 1.6 mmol) and EDCI (0.31 g, 1.6 mmol). The reaction was stirred for 20 h at room temperature under N2. The reaction mixture was diluted with 50 mL of CH2Cl2, washed with H2O, 10% citric acid, NaHCO3 (saturated), brine, dried over Na2SO4 and concentrated. The crude was purified by column chromatography (hexanes/EtOAc) to give 0.15 g (33% yield) of the target 20 as an off-white solid. MS (APCI) m/z: 333.1 (100%, [M+H]+, 186.0 (35%, [M−147+H]+; HPLC purity: 100%; Anal. Calcd. for C17H17ClN2OS: C, 61.34; H, 5.15; N, 8.42; Cl, 10.65; S, 9.63. Found: C, 61.04; H, 5.28; N, 8.36; Cl, 10.78; S, 9.68.

Workup

  1. washwashed with H2O, 10% citric acid, NaHCO3 (saturated), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude was purified by column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-55c84f8197eb4155a98052b7bcf2ab39
Source dataset
uspto-grants-2011_08
Patent number
US07998980B2

Reaction notes

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