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

HRID 1178026

반응식

HRID 1178026 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-360865b54a30464680bd93d3e8b49265
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

연결된 노트

불러오는 중…