Hydrochloric Acid → 3-[5-(1-Quinolin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

HRID 1791366ノート

反応式

HRID 1791366 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[N:8]=1.Cl.Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C.CCOCC.O>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[N:8]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

生成物 1

HCID 100692683-[5-(1-Quinolin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (50.8 mg, 0.2 mmol) was mixed with 2-(chloromethyl)quinoline monohydrochloride (47.1 mg, 0.22 mmol) and diisopropylethylamine (129.3 mg, 1.0 mmol) in DMF (2 mL) at 80° C. for 20 h. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried with sodium sulfate, purified by column chromatography with 5˜10% ethyl acetate in hexanes to give a colorless sticky oil. This sticky oil was mixed with 1 M HCl in ether (0.4 mL) and triturated with ethyl acetate to give an off-white solid, 45 mg (48%). 1H NMR (CDCl3+DMSO-d6), δ(ppm): 8.92 (d, 1H), 8.70 (d, 1H), 8.16 (m, 3H), 8.07 (d, 1H), 8.00 (t, 1H), 7.84 (m, 2H), 7.63 (m, 1H), 4.64 (m, 3H), 3.30 (m, 1H), 2.86(m, 1H), 2.04–2.38 (m, 2H), 1.57–1.90 (m, 4H).

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. custompurified by column chromatography with 5˜10% ethyl acetate in hexanes
  5. customto give a colorless sticky oil
  6. customtriturated with ethyl acetate
  7. customto give an off-white solid, 45 mg (48%)

出典と根拠

ORDレコード
ord-6ab5f886a86e44dfae5f95c005cece48
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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