1-Hydroxybenzotriazole → HCID 57874499, 화합물

HRID 1093702노트

반응식

HRID 1093702 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.[O:43]1[CH:47]=[N:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)=[N: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:54][C:51]2[CH:50]=[CH:49][C:48]([C:45]3[N:46]=[CH:47][O:43][N:44]=3)=[CH:53][CH:52]=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 214837044-(1,2,4-Oxadiazol-3-yl)anilineHCID 578744033-[4-(2-Chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid

생성물 1

HCID 57874499HCID 57874499, 화합물수율 61%

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 (0.1 g, 0.00034 mole) in DMF (2 mL) was added DMAP (0.063 g, 0.00051 mole), HOBt (0.055 g, 0.00041 mole) and EDCI.HCl (0.079 g, 0.00041 mole). After 2 minutes 4-[1, 2, 4]-oxadiazol-3-yl-phenylamine (0.06 g, 0.00037 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. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to afford 0.09 g (61%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-N-(4-[1,2,4]oxadiazol-3-yl-phenyl)-3-oxo-propionamide. LC-MS purity: 441 (M+1)+, 94.4%, 1H NMR (CDCl3): δ 10.5 (s, 1H), 8.8 (s, 1H), 8.1 (d, 2H), 7.74 (d, 2H), 7.4 (d, 1H), 7.2 (d, 1H), 6.96 (t, 2H), 4.7 (q, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.6 (m, 2H), 3.55 (s, 2H), 2.0 (m, 5H).

후처리

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5de2b33eee0a4b599f217631ef985cfe
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

반응 노트

불러오는 중…