1-Hydroxybenzotriazole → HCID 86634608, 화합물

HRID 1665647노트

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HRID 1665647 반응식
C1C=CC2N(O)N=[N:7]C=2C=1.[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[CH2:19][CH2:18]1)[CH2:13][C:14](O)=[O:15].CCN=C=NCCCN(C)C.Cl.O1C=NC(C2C=CC(N)=CC=2)=N1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[CH2:19][CH2:18]1)[CH2:13][C:14]([NH2:7])=[O:15]

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineHCID 57875813HCID 57875813, 화합물

생성물 1

HCID 86634608HCID 86634608, 화합물

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
10 °C

실험 절차

HOBt (49 mg, 0.36 mmol) and DMAP (55 mg, 0.45 mmol) were added to a stirred solution of 3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.3 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (69 mg, 0.36 mmol) followed by 4-[1,2,4]-oxadiazol-3-yl-phenylamine (53 mg, 0.33 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using silica 60-120 mesh (30% ethyl acetate in hexane) to afford 15 mg (11%) of N-(4-[1,2, and 4]oxadiazol-3-yl-phenyl)-3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 474.13 (M+1)+, 98.2%, 1H NMR: (DMSO-d6): δ 10.5 (s, 1H), 9.7 (s, 1H), 8.0 (d, 2H), 7.8 (d, 2H), 7.5 (t, 2H), 3.6 (m, 10H).

후처리

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1e716230d05c4ab2a2cf33c6cf3448d7
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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