1-Hydroxybenzotriazole → 4-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 1178065

反応式

HRID 1178065 の反応式
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:30]=[CH:29][C:21]([C:22]([NH:24][CH2:25][C:26]([OH:28])=O)=[O:23])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:54]1([C:60]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]([F:71])([F:70])[F:69])=[O:61])[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1>CN(C=O)C.O>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][CH2:25][C:26](=[O:28])[N:57]2[CH2:58][CH2:59][N:54]([C:60](=[O:61])[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=3[C:68]([F:71])([F:69])[F:70])[CH2:55][CH2:56]2)=[O:23])=[CH:29][CH:30]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 23931762{[4-(Benzyloxy)phenyl]formamido}acetic acid

生成物 1

HCID 578556614-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide収率 104.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (98 mg, 0.76 mmol) was added to a stirred solution of (4-benzyloxy-benzoylamino]-acetic acid (50 mg, 0.17 mmol) in DMF (3 mL). HOBT (25.8 mg, 0.19 mmol) and EDCI.HCl (83 mg, 0.43 mmol) were added at room temperature. After 2 minutes, piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (61.5 mg, 0.21 mmol). The resulting mixture was stirred at room temperature overnight. The mixture was diluted with cold water and the resulting precipitate was filtered, washed with hexane and dried to afford 93 mg (99% yield) of 4-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LC-MS purity: 87%, 1H NMR (DMSO): δ 8.5 (s, 1H,), 7.8 (m, 5H), 7.5 (s, 1H), 7.4 (m, 4H), 7.1 (d, 2H), 5.2 (s, 2H), 4.2 (d, 2H), 3.7 (m, 4H), 3.5 (s, 2H), 3.4 (s, 2H), 3.3 (s, 2H).

後処理

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with hexane
  3. customdried

出典と根拠

ORDレコード
ord-6302d29bbce141e88cc21d9c1039d7ef
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

関連ノート

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