Trifluoroacetic acid → HCID 57855674, compound

HRID 1177849Notes

Reaction equation

HRID 1177849 reaction equation
CCN(C(C)C)C(C)C.C(O[C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)=[CH:20][CH:19]=1)C1C=CC=CC=1.CCN=C=NCCCN(C)C.[CH:45]1[CH:46]=[CH:47][C:48]2N(O)N=N[C:49]=2[CH:50]=1.[NH2:55][CH2:56][C:57]([N:59]1[CH2:64][CH2:63][N:62]([C:65](=[O:76])[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=2[C:72]([F:75])([F:74])[F:73])[CH2:61][CH2:60]1)=[O:58].[C:77](O)(C(F)(F)F)=[O:78]>CN(C=O)C.O>[CH2:77]([O:78][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:55][CH2:56][C:57](=[O:58])[N:59]3[CH2:60][CH2:61][N:62]([C:65](=[O:76])[C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=4[C:72]([F:75])([F:73])[F:74])[CH2:63][CH2:64]3)=[O:29])=[CH:30][CH:31]=2)=[CH:20][CH:19]=1)[C:49]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:50]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22484919HCID 22484919, compoundHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 57855674HCID 57855674, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.084 mL, 0.49 mmol) was added dropwise to 4-(4-benzyloxy-phenoxy)-benzoic acid (62 mg, 0.20 mmol) in DMF (4 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 added and the resulting solid was isolated by filtration to afford 80 mg (80% yield) of 4-(4-benzyloxy-phenoxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide.

Workup

  1. customthe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-3dd017ee8e024b6983cd38b1938709f9
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…