Trifluoroacetic acid → 4-benzenesulfonyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide
Reaction equation
CCN(C(C)C)C(C)C.[C:10]1([S:16]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:49][CH2:50][C:51]([N:53]1[CH2:58][CH2:57][N:56]([C:59](=[O:70])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])[CH2:55][CH2:54]1)=[O:52].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[C:10]1([S:16]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:49][CH2:50][C:51](=[O:52])[N:53]3[CH2:54][CH2:55][N:56]([C:59](=[O:70])[C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=4[C:66]([F:67])([F:69])[F:68])[CH2:57][CH2:58]3)=[O:25])=[CH:26][CH:27]=2)(=[O:17])=[O:18])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
DIPEA (0.084 mL, 0.49 mmol) was added drop wise to 4-benzenesulfonyl-benzoic acid (51 mg, 0.20 mmol) in DMF (5 mL). EDCI (78 mg, 0.41 mmol) and HOBT (26 mg, 0.20 mmol) were added consecutively and, after 10 mins, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its TFA salt form (70 mg, 0.16 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added and the resulting solid was filtered to afford 60 mg (65% yield) of 4-benzenesulfonyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LC-MS purity: 95.5%. 1H NMR (DMSO-D6): δ 8.8 (t, 1H), 8.1 (m, 5H), 7.8 (m, 6H), 7.6 (m, 1H), 4.2 (d, 2H), 3.6 (m, 6H), 3.2 (m, 2H).
Workup
- filtrationthe resulting solid was filtered
Sources & evidence
- ORD record
- ord-22a7381818564c6cadffdc0d16d7805b
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842696B2
Reaction notes
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