3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 54766236, 화합물

HRID 1044069

반응식

HRID 1044069 반응식
[Cl:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[C:14]1([CH:20]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C.C(OCC)(=O)C>[Cl-:1].[C:8]1([C:6]2[O:5][N:4]=[C:3]([CH2:2][N+:26]34[CH2:27][CH2:28][CH:29]([CH2:30][CH2:31]3)[C@@H:24]([O:23][C:21](=[O:22])[CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[CH2:25]4)[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

생성물 1

HCID 54766236HCID 54766236, 화합물수율 19.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (79 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate (I23) (129 mg, 0.37 mmol) in acetonitrile (1.2 ml) and ethyl acetate (2.4 ml). The yellow solution was stirred at room temperature for 48 hours. The solution was evaporated, and the residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-phenyl-2-(o-tolylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (39 mg, 19% yield, mixture of diastereomers).

후처리

  1. customThe solution was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-e0eddd1fcbfc4ded98c93537f94d1c73
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563577B2

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