3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 54766236、化合物

HRID 1044069

反応式

HRID 1044069 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 54766236HCID 54766236、化合物収率 19.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e0eddd1fcbfc4ded98c93537f94d1c73
出典データセット
uspto-grants-2013_10
特許番号
US08563577B2

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