Trifluoroacetic acid → HCID 59559642, compound

HRID 1177852Notes

Reaction equation

HRID 1177852 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:69])[C:58]2[CH:63]=[C:62]([F:64])[CH:61]=[CH:60][C:59]=2[C:65]([F:68])([F:67])[F:66])[CH2:53][CH2:52]1)=[O:50].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[F:64][C:62]1[CH:61]=[CH:60][C:59]([C:65]([F:67])([F:66])[F:68])=[C:58]([CH:63]=1)[C:57]([N:54]1[CH2:55][CH2:56][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)[CH2:52][CH2:53]1)=[O:69]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2923314-(Phenylamino)benzoic acidHCID 595595982-Amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 59559642HCID 59559642, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (133 mg, 0.18 mL, 0.56 mmol) was added drop wise to 4-phenylamino-benzoic acid (preparation as described above) (75 mg, 0.35 mmol) in DMF (5 mL). EDCI (167 mg, 0.87 mmol) and HOBT (56 mg, 0.42 mmol) were added. After 10 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its TFA salt form (187 mg, 0.42 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated to afford 87 mg (47% yield) of N-{2-[4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 88.27%. 1H-NMR (DMSO-D6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.9 (m, 1H), 7.8 (d, 2H), 7.6 (m, 2H), 7.3 (t, 2H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (t, 1H), 4.2 (d, 2H), 3.8 (m, 4H), 3.6 (m, 2H), 3.2 (m, 2H), 3.1 (m, 1H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-5b881d4eb2b943e1b3e52bc2a1c0eae1
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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