1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523544, compound

HRID 1177906Notes

Reaction equation

HRID 1177906 reaction equation
CCN(C(C)C)C(C)C.Cl.[NH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:17][CH2:16]1)=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[OH:54][C:55]1[CH:63]=[CH:62][C:58]([C:59](O)=[O:60])=[CH:57][N:56]=1>CN(C=O)C.O>[OH:54][C:55]1[CH:63]=[CH:62][C:58]([C:59]([NH:11][CH2:12][C:13](=[O:14])[N:15]2[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:29])[F:30])[CH2:19][CH2:20]2)=[O:60])=[CH:57][N:56]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochlorideHCID 178418479HCID 178418479, compound

Product 1

HCID 178523544HCID 178523544, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (418 mg, 0.56 mL, 3.2 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (303.4 mg, 0.86 mmol) in DMF (4 mL). HOBT (106 mg, 0.79 mmol) and EDCI (344 mg, 1.7 mmol) were then added at room temperature. After 2 minutes, 6-hydroxy nicotinic acid (100 mg, 0.71 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by preparative HPLC to afford 77 mg (24.6% yield) of 6-hydroxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-nicotinamide. LCMS Purity: 95.26%. 1H NMR (DMSO-d6): δ 12 (s, 1H), 8.4 (s, 1H), 7.9-7.74 (m, 3H), 7.72-7.62 (m, 1H), 7.6-7.5 (m, 1H), 4.2-4.0 (d, 2H), 3.9-3.52 (m, 5H), 3.24-3.0 (m, 3H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-03e17e0ef4a24e58bfb8ddb0d6a9bc99
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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