Sodium hydride → Ethyl 8-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 732155

반응식

HRID 732155 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]3[CH2:12][CH2:13][CH2:14][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]3=[N:9][N:8]=2)=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH:24]([C:26]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)[O:28][N:27]=1)[CH3:25].[NH4+].[Cl-]>CN(C=O)C>[Cl:37][C:33]1[CH:32]=[C:31]([C:29]2[O:28][N:27]=[C:26]([CH:24]([C:15]3([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][N:11]4[C:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)=[N:8][N:9]=[C:10]34)[CH3:25])[N:30]=2)[CH:36]=[CH:35][CH:34]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 578379793-(1-Chloroethyl)-5-(3-chlorophenyl)-[1,2,4]oxadiazoleHCID 57837993Ethyl 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

생성물 1

HCID 57837930Ethyl 8-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
65 °C

실험 절차

A solution of ethyl 3-pyridin-4-yl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (182 mg, 0.67 mmol) in DMF (2 ml) was added to a stirred mixture of NaH (20 mg, 0.81 mmol) in DMF (2 ml). After 45 min a solution of 3-(1-chloroethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (180 mg, 0.74 mmol) in DMF (1 ml) was added and the resulting solution was stirred at 65° C. for 3 h and then cooled to r.t. Aq. sat. NH4Cl solution was added and the mixture was extracted with EA. The organic phase was washed with water and brine, dried and concentrated. Column chromatography (DCM/MeOH 20:1) gave 207 mg (65%) of the title compound as a diastereomeric mixture. 1H NMR: 1.27 (t, 3 H), 1.34 (t, 3 H), 1.48 (d, 3 H), 1.55 (d, 3 H), 2.15 (m, 2 H), 2.18 (m, 4 H), 2.61 (m, 2 H), 4.00 (m, 2 H), 4.18-4.29 (m, 4 H), 4.30-4.40 (m, 2 H), 4.55 (q, 1 H), 4.65 (q, 1 H), 7.37 (t, 1 H), 7.44 (t, 1 H), 7.50 (m, 1 H), 7.55 (m, 1 H), 7.63 (d, 2 H), 7.69 (d, 2 H), 7.83 (m, 1 H), 7.92 (m, 1 H), 7.95 (m, 1 H), 8.05 (m, 1 H), 8.75 (d, 2H), 8.76 (d, 2 H)

후처리

  1. temperaturecooled to r.t
  2. extractionthe mixture was extracted with EA
  3. washThe organic phase was washed with water and brine
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a0abfb1b73b4719826cee905499bceb
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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