1,2-Dichloroethane → n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-methoxy-phenyl)-propionamide

HRID 413420Notes

Reaction equation

HRID 413420 reaction equation
[NH2:1][C:2]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([F:18])[CH:11]=1)([C:4]1[N:5]([CH3:9])[CH:6]=[N:7][CH:8]=1)[CH3:3].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][C:29](O)=[O:30])[CH:24]=[CH:25][CH:26]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([C:2]([NH:1][C:29](=[O:30])[CH2:28][CH2:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=2)([C:4]2[N:5]([CH3:9])[CH:6]=[N:7][CH:8]=2)[CH3:3])=[CH:11][C:12]=1[F:18])#[N:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 663363-(m-Methoxyphenyl)propionic acidHCID 181649HOAtHCID 11470581(+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile

Product 1

HCID 18533208n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-methoxy-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile (0.074 g, 0.25 mmol), 3-(3-methoxyphenyl)propionic acid (0.054 g, 0.3 mmol) (K. J. Hwang et al., J. Org. Chem. (1992), 57[4]1262), EDC (0.275 g, 1.2 mmol), HOAT (0.055 g, 0.40 mmol), and triethylamine (0.167 mL, 1.2 mmol) were combined in DMF (3 mL) and stirred under Ar at ambient temperature for 20 hr. The reaction mixture was partitioned between EtOAc (120 mL) and H2O (100 mL), the organic layer separated, washed with dilute NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (120 mL) and H2O (100 mL)
  2. customthe organic layer separated
  3. washwashed with dilute NaHCO3 solution, H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-d5167fbe92f24550a640564382e60338
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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