1-Hydroxybenzotriazole → HCID 25165130, compound

HRID 1178052Notes

Reaction equation

HRID 1178052 reaction equation
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]1)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:61]1([C:67]2[O:71][C:70]([C:72](O)=[O:73])=[CH:69][CH:68]=2)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C=O)C.O>[O:20]=[C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]1)[CH2:18][NH:17][C:72]([C:70]1[O:71][C:67]([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)=[CH:68][CH:69]=1)=[O:73]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7362555-Phenylfuran-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Product 1

HCID 25165130HCID 25165130, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (82 mg, 0.109 mL, 0.64 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt, (109 mg, 0.26 mmol) in DMF (1 mL). HOBT (34 mg, 0.26 mmol) and EDCI.HCl (49 mg, 0.26 mmol) were added at room temperature. After 2 minutes 5-phenyl furoic acid (40 mg, 0.21 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 45 mg (40% yield) of 5-phenyl-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity %: 84.97, HPLC Purity: 92.51%, 1H NMR (DMSO-d6): δ 8.6 (t, 1H), 8.0-7.9 (d, 2H) 7.9-7.6 (m, 3H), 7.6-7.5 (bt, 1H), 7.5 (t, 2H), 7.4-7.3 (m, 1H), 7.2 (m, 1H), 7.1 (d, 1H), 4.2-4.1 (m, 2H), 3.8-3.5 (m, 4H), 3.4 (m, 2H), 3.2-3.1 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19a849ea953749398c1a9c0ab5d20d8d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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