Hydrochloric Acid → N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-6-phenylamino-nicotinamide

HRID 1177861Notes

Reaction equation

HRID 1177861 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([NH:16][C:17]2[N:22]=[CH:21][C:20]([C:23]([OH:25])=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:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:53][CH2:52]1)=[O:50].Cl>CN(C=O)C.O>[O:50]=[C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:55][CH2:56]1)[CH2:48][NH:47][C:23](=[O:25])[C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:22][CH:21]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27718126-(Phenylamino)nicotinic acidHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 59559675N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-6-phenylamino-nicotinamideYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (126 mg, 0.17 mL, 0.98 mmol) was added drop wise to 6-(phenyl-amino)-pyridine-3-carboxylic acid (70 mg, 0.32 mmol) in DMF (5 mL). EDCI (74 mg, 0.39 mmol) and HOBT (53 mg, 0.39 mmol) were added consecutively and, after 10 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (137 mg, 0.39 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 110 mg (65% yield) of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-6-phenylamino-nicotinamide. LC-MS purity: 93.71%. 1H-NMR (DMSO-d6): δ 9.4 (s, 1H), 8.7 (s, 1H), 8.5 (t, 1H), 8.0 (d, 1H), 7.8 (m, 2H), 7.7 (d, 3H), 7.6 (m, 1H), 6.9 (t, 1H), 6.8 (d, 1H), 4.2 (dd, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-7a38603f573c415eb2e3bf2ce50ff2d8
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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