4-Fluorobenzoic Acid → HCID 59559577, compound

HRID 1177951Notes

Reaction equation

HRID 1177951 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.[F:61][C:62]1[CH:70]=[CH:69][C:65]([C:66](O)=[O:67])=[CH:64][CH:63]=1>CN(C=O)C.O>[F:61][C:62]1[CH:70]=[CH:69][C:65]([C:66]([NH:17][CH2:18][C:19](=[O:20])[N:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]2)=[O:67])=[CH:64][CH:63]=1

Participants

8

Reactant 5

HCID 99734-Fluorobenzoic 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 59559577HCID 59559577, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (46.5 mg, 0.36 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt. (62 mg, 0.14 mmol) in DMF (1 mL). HOBT (19 mg, 0.14 mmol) and EDCI.HCl (28 mg, 0.14 mmol) were then added at room temperature. After 2 minutes, 4-fluorobenzoic acid (17 mg, 0.12 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 34 mg of 4-fluoro-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide LCMS Purity: 92.29%, HPLC Purity: 93.53%. NMR Values: 1H NMR (DMSO-d6): δ 7.9-7.8 (2H, m), 7.8-7.7 (d, 1H), 7.6 (m, 2H), 7.4-7.3 (d, 1H), 7.3 (t, 2H), 4.3 (dd, 1H), 4.2 (dd, 2H), 4.0 (m, 2H), 3.8-3.6 (m, 2H), 3.6-3.5 (m, 2H), 3.4 (t, 1H), 3.3-3.2 (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-70c9287a09834a8a9f987937607e3d90
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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