1-Hydroxybenzotriazole → HCID 57874460, 화합물

HRID 1093688

반응식

HRID 1093688 반응식
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:16])[CH2:12][C:13]([OH:15])=O)[CH2:7][CH2:6]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:43]1([C:49]2[N:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11](=[O:16])[CH2:12][C:13]([NH:55][C:52]2[CH:53]=[N:54][C:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:50][CH:51]=2)=[O:15])[CH2:9][CH2:10]1

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628776-Phenylpyridin-3-amineHCID 57874403HCID 57874403, 화합물

생성물 1

HCID 57874460HCID 57874460, 화합물수율 53%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.08 g, 0.00027 mole) in DMF (3 mL) was added DMAP (0.049 g, 0.00040 mole), HOBt (0.043 g, 0.00032 mole) and EDCI.HCl (0.06 g, 0.00032 mole). After 2 minutes 6-phenyl-pyridin-3-ylamine (0.055 g, 0.00032 mole) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.0642 g (53%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LC-MS purity: 450.15 (M+1)+, 99.25%, 1H NMR (DMSO-d6): δ 10.4 (s, 1H), 8.8 (s, 1H), 8.2 (dd, 1H), 8.1-8.0 (m, 2H), 8.0-7.9 (m, 1H), 7.5-7.2 (m, 6H), 7.0-6.9 (m, 1H), 4.8-4.7 (m, 1H), 3.8-3.7 (m, 2H), 3.7-3.6 (s, 2H), 3.6-3.5 (m, 2H), 2.1-1.5 (m, 4H).

후처리

  1. extractionthe product was extracted with ethyl acetate ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-29c0be9450ca46059b41a909b6b04a31
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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