(1,1'-Biphenyl)-4-carboxylic acid → HCID 25164523, compound

HRID 1177958Notes

Reaction equation

HRID 1177958 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:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:66]=[CH:65][C:64]([C:67](O)=[O:68])=[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:67]([C:64]1[CH:65]=[CH:66][C:61]([C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)=[CH:62][CH:63]=1)=[O:68]

Participants

8

Reactant 5

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 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 25164523HCID 25164523, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (48 mg, 0.38 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (87 mg, 0.20 mmol) in DMF (1 mL). HOBT (19 mg, 0.15 mmol) and EDCI.HCl (29 mg, 0.15 mmol) were then added at room temperature. After 2 minutes, biphenyl-4-carboxylic acid (25 mg, 0.13 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water (20 mL) 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 afford 26 mg (42% yield) of biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 94.87%, HPLC Purity: 97.28%, 1H NMR (DMSO-d6): δ 8.6 (bs, 1H), 8.0-7.9 (d, 2H), 7.8-7.6 (m, 7H), 7.6-7.4 (m, 4H), 4.2 (d, 2H), 3.8-3.6 (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 materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9955547097c541b7b1bf25af3419f8da
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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