Picolinic acid → Pyridine-2-carboxylic Acid [2-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide

HRID 496411노트

반응식

HRID 496411 반응식
[NH2:1][C:2]1[C:11]([O:12][C@@H:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:26].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](O)=[O:34].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:15]1([CH2:14][C@H:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7](=[O:26])[CH2:6][CH2:5][CH2:4][C:3]=3[C:2]=2[NH:1][C:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=2)=[O:34])[CH:19]=[CH:18][N:17]=[CH:16]1

참가 물질

7

반응물 5

HCID 1018Picolinic acidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 600298675-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 60029899Pyridine-2-carboxylic Acid [2-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (150 mg, 0.432 mmol), picolinic acid (64 mg, 0.518 mmol) and HOBT (73 mg, 0.540 mmol) in DMF (4 mL) was added N-methylmorpholine (62 μL, 0.562 mmol) followed by EDCI HCl (108 mg, 0.562 mmol). After 2 days, the DMF was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O and brine, dried over Na2SO4 and concentrated to give a brown oil. Purification by chromatography (3-5% MeOH/CH2Cl2) afforded the title compound as a tan foam (160 mg, 0.354 mmol, 82%). The structure was confirmed by NMR and mass spectrometry. MS m/z 453 (M++H).

후처리

  1. customthe DMF was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customPurification by chromatography (3-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-e86fb60c60bf4c65859beedde765adc2
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943183B2

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