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

HRID 1178028

反応式

HRID 1178028 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  1. filtrationthe resulting solid was filtered under reduced pressure

出典と根拠

ORDレコード
ord-c7d7fbd00dd14ec9a67834450ee3a95d
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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