1,2-Dichloroethane → HCID 86667492, compound

HRID 333917Notes

Reaction equation

HRID 333917 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[S:14][C:13]([NH2:15])=[N:12][CH:11]=2)=[CH:5][CH:4]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH2:23][C:24](O)=[O:25])[CH:17]=1.CCN(CC)CC.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[S:14][C:13]([NH:15][C:24](=[O:25])[CH2:23][CH2:22][C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)=[N:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2596243-(Pyridin-3-yl)propanoic acidHCID 8829822HCID 8829822, compound

Product 1

HCID 86667492HCID 86667492, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-methoxy-phenylsulfanyl)-thiazol-2-ylamine (70b, 3.0 g, 12.6 mmol), 3-pyridin-3-yl-propionic acid (2.30 g, 15.1 mmol), NEt3 (6.10 ml, 44.1 mmol), EDC (4.80 g, 25.2 mmol) and HOBt (3.40 g, 25.2 mmol) in DMF (150 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure to give N-[5-(4-methoxy-phenylsulfanyl)-thiazol-2-yl]-3-pyridin-3-yl-propionamide (70, 3.50 g) in 75% yield: 1H NMR (500 MHz, DMSO) δ 8.45 (d, 1H), 8.39 (m, 1H), 7.64 (m, 2H), 7.29 (m, 3H), 6.92 (t, 2H), 3.73 (t, 3H), 2.90 (t, 2H), 2.77 (t, 2H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11468f60f4614e0c847f8c684a34757b
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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