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

HRID 1060883노트

반응식

HRID 1060883 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a812b670a83421bb69e7bd9d44c305a
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525074B2

반응 노트

불러오는 중…