Triethylamine → HCID 52559791, compound

HRID 333915Notes

Reaction equation

HRID 333915 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[S:12][C:11]([NH2:13])=[N:10][CH:9]=2)=[CH:5][CH:4]=1.N1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH2:23][C:24]([OH:26])=O)[CH:17]=1.[CH:27]1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[S:12][C:11]([NH:13][C:24](=[O:26])[CH2:23][CH2:22][C:18]3[CH:17]=[CH:27][CH:21]=[CH:20][CH:19]=3)=[N:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2596243-(Pyridin-3-yl)propanoic acidHCID 31330525-(4-Methoxy-benzyl)-thiazol-2-ylamine

Product 1

HCID 52559791HCID 52559791, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(4-methoxy-benzyl)-thiazol-2-ylamine (9d, 1.0 g, 4.54 mmol) and 3-pyridin-3-yl-propionic acid (0.92 g, 5.45 mmol), EDCA (1.74 g, 9.08 mmol), HOBt (1.23 g, 9.08 mmol) and NEt3 (1.38 g, 13.6 mmol) in DMF (15.0 mL) was stirred for 16 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-[5-(4-methoxy-benzyl)-thiazol-2-yl]-3-phenyl-propionamide (9, 1.05 g) in 66% yield: 1H NMR (500 MHz, CDCl3) δ 7.27 (d, 2 H), 7.3-7.15 (m, 6 H), 6.86 (d, 2 H), 3.98 (s, 2 H), 3.72 (s, 3 H), 2.87 (m, 2 H), 2.64 (m, 2 H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ef03490d32634078ab789779af2152a8
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

Loading…