4-Methylmorpholine → N-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-3-(3-methoxy-benzenesulfonylamino)-propionamide

HRID 1060883Notes

Reaction equation

HRID 1060883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=O)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:48][C:49]([C:57]1[CH:64]=[CH:63][C:60]([C:61]#[N:62])=[C:59]([F:65])[CH:58]=1)([C:51]1[N:52]([CH3:56])[CH:53]=[N:54][CH:55]=1)[CH3:50]>CN(C=O)C>[C:61]([C:60]1[CH:63]=[CH:64][C:57]([C:49]([NH:48][C:15](=[O:17])[CH2:14][CH2:13][NH:12][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:10])=[O:11])([C:51]2[N:52]([CH3:56])[CH:53]=[N:54][CH:55]=2)[CH3:50])=[CH:58][C:59]=1[F:65])#[N:62]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11470581(+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrileHCID 186294403-(3-Methoxy-benzenesulfonylamino)-propionic acid

Product 1

HCID 18629422N-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-3-(3-methoxy-benzenesulfonylamino)-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-methoxy-benzenesulfonylamino)-propionic acid (0.261 g, 1.01 mmol) in DMF (4 mL) at room temperature was added 1-hydroxybenzotriazole hydrate (HOBT) (0.146 g, 0.96 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (0.202 g, 1.05 mmol), 4-methylmorpholine (0.102 g, 1.01 mmol), and (+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile (Step I) (0.246 g, 1.01 mmol). After stirring overnight, the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and water, the organic layer separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the title compound after purification by chromatography on silica gel (5% to 7.5% methanol/0.1% ammonium hydroxide in CH2Cl2).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a812b670a83421bb69e7bd9d44c305a
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

Loading…