1-Hydroxybenzotriazole → HCID 86634608、化合物

HRID 1665647ノート

反応式

HRID 1665647 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 86634608HCID 86634608、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e716230d05c4ab2a2cf33c6cf3448d7
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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