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

反応式

HRID 732155 の反応式
[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

参加物

6

反応物 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

生成物 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-carboxylate収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
65 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-6a0abfb1b73b4719826cee905499bceb
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

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