Morpholine → N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide

HRID 1845760노트

반응식

HRID 1845760 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13]([CH2:17][CH2:18][CH2:19]CS([O-])(=O)=O)=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].CCN(C(C)C)C(C)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13]([CH2:17][CH2:18][CH2:19][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 866141833-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propylmethanesulfonate

생성물 1

HCID 58941763N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide수율 54%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

3-(4-[(3-Chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propylmethanesulfonate (19 mg, 0.051 mmol) was dissolved in anhydrous ACN (100 μL) followed by addition of DIPEA (44 μL, 0.26 mmol) and morpholine (6.7 μL, 76.8 μmol). The reaction was stirred and heated at 70° C. for 3 h. The reaction was concentrated and purified with silica gel chromatography (60-100% ethyl acetate/hex) to give the desired product (10 mg, 54%). LCMS for C16H19ClFN4O3(M+H)+: m/z=369.1.

후처리

  1. concentrationThe reaction was concentrated
  2. custompurified with silica gel chromatography (60-100% ethyl acetate/hex)

출처 및 근거

ORD 기록
ord-6b2edba48de8400c915d17af1a45eb21
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951536B2

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