1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-one

HRID 1016118ノート

反応式

HRID 1016118 の反応式
[CH3:1][CH:2]([CH3:19])[CH:3]([NH:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:12]=1)[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.Cl.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CO>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:40][CH2:41][N:42]([C:4](=[O:6])[CH:3]([NH:7][C:8]3[O:9][C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][N:12]=3)[CH:2]([CH3:1])[CH3:19])[CH2:43][CH2:44]2)=[CH:35][CH:34]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27578434-(4-chlorophenyl)piperidine HydrochlorideHCID 578892573-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid

生成物 1

HCID 578889751-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-one収率 45.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

3-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid (80 mg, 0.3 mmol), EDCI (65 mg, 0.33 mmol), 4-(4-chlorophenyl)-piperidine hydrochloride (78 mg, 0.33 mmol) and HOBt (40 mg, 0.3 mmol) were combined and suspended in DMF (2 mL). Diisopropylethylamine (210 μL, 1.2 mmol) was added and the reaction was stirred at rt. overnight. After this time, methanol (2 mL) was added to the reaction and the mixture was purified directly by preparative HPLC to give 1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-one (60 mg, 30%). MS found: 439 (M+H).

後処理

  1. customovernight
  2. customthe mixture was purified directly by preparative HPLC

出典と根拠

ORDレコード
ord-6dc654f369664d92b996facb1d28cdda
出典データセット
uspto-grants-2011_07
特許番号
US07985861B2

反応ノート

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