2-Methylbenzoic acid → N-{2-[4-(2-Methyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide
Reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:41]=[C:42]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)[CH2:43][NH:44][C:45](=[O:59])[C:46]1[CH:51]=[CH:50][C:49]([O:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:48][CH:47]=1>CN(C=O)C.O>[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([N:63]1[CH2:64][CH2:65][N:60]([C:42](=[O:41])[CH2:43][NH:44][C:45](=[O:59])[C:46]2[CH:47]=[CH:48][C:49]([O:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[CH:50][CH:51]=2)[CH2:61][CH2:62]1)=[O:15]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
DIPEA (0.091 mL, 0.53 mmol) was added drop wise to 2-Methyl benzoic acid (23 mg, 0.2123 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. The residue was dissolved in methylene chloride and filtered to afford N-{2-[4-(2-Methyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide in 36% yield. LC-MS purity: 98%, 1H NMR (DMSO-D6): δ 8.5 (d, 1H), 7.9 (d, 2H), 7.4 (t, 2H), 7.2 (m, 5H), 7.1 (q, 4H), 4.2 (2d, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H), 2.2 (s, 3H).
Workup
- filtrationthe resulting solid was filtered under reduced pressure
- dissolutionThe residue was dissolved in methylene chloride
- filtrationfiltered
Sources & evidence
- ORD record
- ord-f4156feea55543a3a3b1b58af260c1e1
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842696B2
Reaction notes
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