1-Hydroxybenzotriazole → HCID 178523501, 화합물

HRID 1093608노트

반응식

HRID 1093608 반응식
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N+:51]([C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)([O-:53])=[O:52]>CN(C=O)C.O>[N+:51]([C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH:57]1[CH2:62][CH2:61][N:60]([C:16](=[O:18])[CH2:15][NH:14][C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][N:10]=2)=[O:13])[CH2:59][CH2:58]1)([O-:53])=[O:52]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 467391574-(2-Nitrophenoxy)piperidine hydrochlorideHCID 178525878HCID 178525878, 화합물

생성물 1

HCID 178523501HCID 178523501, 화합물수율 44%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.15 g, 0.0006 mol) in DMF (3 mL) was added DIPEA (0.27 g, 0.0021 mol), HOBt (0.12 g, 0.0009 mol) and EDCI.HCl (0.17 g, 0.0009 mol) at ambient temperature. After 2 minutes 4-(2-nitro-phenoxy)-piperidine hydrochloride (0.19 g, 0.00073 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The product was extracted with ethyl acetate, and the organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using neutral aluminium oxide (5% methanol in chloroform) to afford 0.1 g (44%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-nitro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 450.17 (M+1)+, 96.5%, 1H NMR (DMSO-d6): δ 8.1 (bs, 1H), 7.9 (m, 3H), 7.6 (m, 1H), 7.5 (m, 4H), 7.1 (m, 2H), 5.0 (m, 1H), 4.2 (m, 2H), 3.8 (m, 8H), 2.0 (m, 2H).

후처리

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-f25ae17f766d414da33af8fe818177cf
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

반응 노트

불러오는 중…