Trifluoroacetic acid → HCID 59559611, compound

HRID 1177855Notes

Reaction equation

HRID 1177855 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:66])[C:58]2[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=2[Cl:65])[CH2:53][CH2:52]1)=[O:50].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[Cl:65][C:59]1[CH:60]=[CH:61][C:62]([Cl:64])=[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:66]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2923314-(Phenylamino)benzoic acidHCID 595595792-Amino-1-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 59559611HCID 59559611, compoundYield 78%

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-(2,5-dichloro-benzoyl)-piperazin-1-yl]-ethanone in its TFA salt form (148 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 140 mg (78% yield) of N-{2-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 95.65%. 1H-NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (m, 5H), 7.3 (t, 2H), 7.2 (m, 4H), 6.9 (t, 1H), 4.1 (d, 2H), 3.6 (m, 6H), 3.2 (d, 2H).

Workup

  1. filtrationfiltered the solid

Sources & evidence

ORD record
ord-f3ca1f0b12354be7aaab5e882661ed32
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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