1-Hydroxybenzotriazole → N-{2-[4-(2-Bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide

HRID 1178026

反応式

HRID 1178026 の反応式
CCN(C(C)C)C(C)C.[O:10]=[C:11]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH2:12][NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[Br:57][C:58]1[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][C:59]=1[C:60](O)=[O:61]>CN(C=O)C.O>[Br:57][C:58]1[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][C:59]=1[C:60]([N:32]1[CH2:31][CH2:30][N:29]([C:11](=[O:10])[CH2:12][NH:13][C:14](=[O:28])[C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)[CH2:34][CH2:33]1)=[O:61]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 899062-Bromo-5-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59559582N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide

生成物 1

HCID 25165722N-{2-[4-(2-Bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide収率 86.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (85.5 mg, 0.114 mL, 0.66 mmol) was added to a stirred solution of N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide (60 mg, 0.176 mmol) in DMF (2 mL). HOBT (21.89 mg, 0.16 mmol) and EDCI.HCl (70.5 mg, 0.36 mmol) were then added at room temperature. After 2 minutes, 2-Bromo-5-methoxy benzoic acid (33.9 mg, 0.15 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with cold water, and the resulting precipitate was filtered, washed with water then hexane and dried to afford 70 mg (86.5% yield) of N-{2-[4-(2-Bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide as a pale yellow solid. LCMS Purity: 95.76%, HPLC Purity: 96.07%. 1H NMR (CDCl3): δ 8.5 (bs, 1H), 7.9 (d, 2H), 7.5 (m, 1H), 7.4 (m, 2H), 7.2 (m, 1H), 6.9 (m, 5H), 4.2 (m, 2H), 3.8 (s, 3H), 3.5 (m, 6H), 3.2 (m, 2H), 2.1 (s, 1H), 2.0 (m, 1H), 1.3 (s, 3H), 0.8 (m, 1H).

後処理

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. dry with materialhexane and dried

出典と根拠

ORDレコード
ord-360865b54a30464680bd93d3e8b49265
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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