Hydrochloric Acid → HCID 25167124, compound

HRID 1177898Notes

Reaction equation

HRID 1177898 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][NH:11][C:12](=[O:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](O)=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:44][CH2:45][C:46]([N:48]1[CH2:53][CH2:52][N:51]([C:54](=[O:65])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[C:61]([F:64])([F:63])[F:62])[CH2:50][CH2:49]1)=[O:47].Cl>CN(C=O)C.O>[CH3:10][NH:11][C:12](=[O:22])[C:13]1[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([NH:44][CH2:45][C:46](=[O:47])[N:48]2[CH2:49][CH2:50][N:51]([C:54](=[O:65])[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=3[C:61]([F:64])([F:62])[F:63])[CH2:52][CH2:53]2)=[O:17])[CH:14]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 110412933-(methylcarbamoyl)benzoic AcidHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 25167124HCID 25167124, compoundYield 9.18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (330 mg, 0.44 mL, 2.6 mmol) was added drop wise to N-methyl-isophthalamic acid (145 mg, 0.8 mmol) in DMF (3 mL). EDCI (180 mg, 0.96 mmol) and HOBT (130 mg, 0.96 mmol) were added consecutively and, after 10 minutes, 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (281 mg, 0.8 mmol) was added. 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 column chromatography (using basic alumina and 10% MeOH in CHCl3 as eluent) to afford 35 mg (9.18% yield) of N-methyl-N′-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-isophthalamide. LCMS Purity: 97.7%. 1H NMR (CDCl3): δ 8.1 (bs, 1H), 7.9 (m, 2H), 7.7 (m, 1H), 7.5 (m, 3H), 7.4 (m, 2H), 6.3 (bs, 1H), 4.2 (m, 2H), 4.0 (m, 2H), 3.6 (m, 5H), 3.4 (m, 1H), 3.2 (m, 2H), 3.0 (d, 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 column chromatography (using basic alumina and 10% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-5fd732d192c14d6dbef2a2fc5eb3c4a6
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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