Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate → 3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

HRID 1791364ノート

反応式

HRID 1791364 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:15]=1)=O)(C)(C)C>C(O)=O>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=2)[C:25]#[N:26])[N:15]=1

参加物

3

反応物 1

HCID 69619392Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

生成物 1

HCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile収率 77.4%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
45 °C

実験手順

2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (8.1 g) was mixed with 96% formic acid (80 mL) and heated at 45° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organic layer was dried with sodium sulfate and concentrated again. The residue was triturated with hexanes to give 4.5 g (73.4%) of the title compounds as a white solid. 1H NMR (CDCl3), δ(ppm): 8.41 (s, 1H), 8.33 (d, 1H), 7.78 (dd, 1H), 7.61 (t, 1H), 4.15 (dd, 1H), 3.20 (m, 1H), 2.84 (m, 1H), 2.14 (m, 1H), 1.55–2.00 (m, 5H).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was quenched with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated again
  6. customThe residue was triturated with hexanes

出典と根拠

ORDレコード
ord-66a50e87870749f6a6723fc9a87525a5
出典データセット
uspto-grants-2006_07
特許番号
US07074809B2

反応ノート

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