Trifluoroacetic acid → N-{2-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide

HRID 1177856Notes

Reaction equation

HRID 1177856 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:67])[C:58]2[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:59]=2[Br:66])[CH2:53][CH2:52]1)=[O:50].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[Br:66][C:59]1[CH:60]=[CH:61][C:62]([O:64][CH3:65])=[CH:63][C:58]=1[C:57]([N:54]1[CH2:53][CH2:52][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:21](=[O:23])[C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)[CH2:56][CH2:55]1)=[O:67]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2923314-(Phenylamino)benzoic acidHCID 59559614HCID 59559614, compound

Product 1

HCID 59559601N-{2-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamideYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (133 mg, 0.18 mL, 1.0 mmol) was added drop wise to 4-(-phenyl-amino)-benzoic acid (75 mg, 0.35 mmol) in DMF (5 mL). EDCI (167 mg, 0.87 mmol) and HOBT (56 mg, 0.42 mmol) were added consecutively and, after 10 minutes, 2-amino-1-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-ethanone in its TFA salt form (164 mg, 0.42 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid to afford 130 mg (67% yield) of N-{2-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 96.77%. 1H-NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 2H), 7.6 (d, 1H), 7.3 (d, 2H), 7.1 (d, 2H), 7.0 (m, 3H) 4.2 (dd, 2H), 3.8 (s, 3H), 3.6 (m, 6H), 3.2 (m, 2H).

Workup

  1. filtrationfiltered the solid

Sources & evidence

ORD record
ord-38c934017ee14da1b3a85df9e7ba1873
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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