1-Hydroxybenzotriazole → 5-(2-Benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093645ノート

反応式

HRID 1093645 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:19][N:18]=[C:17]([C:20]([NH:22][CH2:23][C:24]([OH:26])=O)=[O:21])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[Cl:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>CN(C=O)C.O>[Cl:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][N:66]([C:24](=[O:26])[CH2:23][NH:22][C:20]([C:17]2[CH:16]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:19][N:18]=2)=[O:21])[CH2:65][CH2:64]1

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167325894-(2-Chlorophenoxy)piperidine hydrochlorideHCID 57874519{[5-(2-Benzyloxy-phenyl)-isoxazole-3-carbonyl]-amino}-acetic acid

生成物 1

HCID 578744145-(2-Benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide収率 73%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of {[5-(2-benzyloxy-phenyl)-isoxazole-3-carbonyl]-amino}-acetic acid (0.15 g, 0.00039 mol) in DMF (2 mL) was added DIPEA (0.224 g, 0.00174 mol), HOBt (0.065 g, 0.000482 mol) and EDCI.HCl (0.0925 g, 0.00048 mol) at ambient temperature. After 5 minutes 4-(2-chloro-phenoxy)-piperidine hydrochloride (0.1 g, 0.00041 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration. Purification by column chromatography using silica gel 230-400 mesh (70% ethyl acetate in hexane) afforded 0.153 g (73%) of 5-(2-benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 546.17 (M+1)+, 97.6%.

後処理

  1. customthe resulting precipitate was isolated by filtration
  2. customPurification by column chromatography

出典と根拠

ORDレコード
ord-0a8cdc56ec6a45688fa753a404290c26
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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