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Trifluoroacetic acid → 4-benzenesulfonyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 1177872
Notes
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Reaction equation

HRID 1177872 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79322Benzoic acid, 4-(phenylsulfonyl)-HCID 81531DiisopropylethylamineHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product

1
HCID 251673254-benzenesulfonyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamideYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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

  1. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-22a7381818564c6cadffdc0d16d7805b
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842696B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes