1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 1178002

Reaction equation

HRID 1178002 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=O)=[O:23])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:55]1([C:61]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])=[O:62])[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1>CN(C=O)C.O>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][C:25]([CH3:30])([CH3:29])[C:26](=[O:28])[N:58]2[CH2:59][CH2:60][N:55]([C:61](=[O:62])[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=3[C:69]([F:72])([F:70])[F:71])[CH2:56][CH2:57]2)=[O:23])=[CH:31][CH:32]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 578556642-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid

Product 1

HCID 595596074-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (284 mg, 0.19 mL, 1.62 mmol) was added to a stirred solution of 2-(4-benzyloxy-benzoylamino)-2-methyl-propionic acid (170 mg, 0.54 mmol) in DMF (2 mL). HOBT (88 mg, 0.65 mmol) and EDCI (125 mg, 0.65 mmol) were then added at room temperature. After 2 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (192 mg, 0.65 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 150 mg (50% yield) of 4-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 93.29%. 1H NMR (DMSO-d6): δ 8.4 (bs, 1H), 7.6-7.8 (m, 5H), 7.4 (m, 6H), 7.0-7.1 (d, 2H), 5.2 (m, 2H), 3.5 (m, 5H), 3.0 (m, 3H), 1.4 (s, 6H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated out

Sources & evidence

ORD record
ord-70f54ed9e03b4e659104debb51e72d80
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

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