Reaction equation
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]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- filtrationthe resulting solid was filtered under reduced pressure
Sources & evidence
- ORD record
- ord-c7d7fbd00dd14ec9a67834450ee3a95d
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842696B2
Linked notes
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