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

HRID 1791366노트

반응식

HRID 1791366 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-6ab5f886a86e44dfae5f95c005cece48
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074809B2

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