2-Furancarboxylic acid → N-{2-[4-(furan-2-carbonyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide

HRID 1178028

반응식

HRID 1178028 반응식
CCN(C(C)C)C(C)C.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([OH:17])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:39]=[C:40]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)[CH2:41][NH:42][C:43](=[O:57])[C:44]1[CH:49]=[CH:48][C:47]([O:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:46][CH:45]=1>CN(C=O)C.O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([N:61]1[CH2:62][CH2:63][N:58]([C:40](=[O:39])[CH2:41][NH:42][C:43](=[O:57])[C:44]2[CH:45]=[CH:46][C:47]([O:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)=[CH:48][CH:49]=2)[CH2:59][CH2:60]1)=[O:17]

참가 물질

8

반응물 5

HCID 69192-Furancarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59559582N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide

생성물 1

HCID 16322921N-{2-[4-(furan-2-carbonyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide수율 65%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (0.091 mL, 0.53 mmol) was added drop wise to furan-2-carboxylic acid (23 mg, 0.21 mmol) in DMF (5 mL). EDCI (84 mg, 0.44 mmol) and HOBT (28 mg, 0.21 mmol) were added consecutively and, after 10 mins, N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide (60 mg, 0.18 mmol) was added and the resulting mixture was stirred at room temperature overnight. Water was then added, and the resulting solid was filtered under reduced pressure to afford N-{2-[4-(furan-2-carbonyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide in 65% yield. LC-MS purity: 92%, 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 8 (t, 3H), 7.4 (t, 2H), 7.2 (t, 1H), 7 (m, 4H), 6.6 (s, 1H), 4.2 (d, 2H), 3.6 (m, 8H).

후처리

  1. filtrationthe resulting solid was filtered under reduced pressure

출처 및 근거

ORD 기록
ord-c7d7fbd00dd14ec9a67834450ee3a95d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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