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

HRID 1060883ノート

反応式

HRID 1060883 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a812b670a83421bb69e7bd9d44c305a
出典データセット
uspto-grants-2003_02
特許番号
US06525074B2

反応ノート

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