Dimethylformamide → HCID 86634607, compound

HRID 1665614Notes

Reaction equation

HRID 1665614 reaction equation
C1C=CC2N([OH:10])N=NC=2C=1.O=C([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]1)CC(O)=O.CCN=C=NC[CH2:41][CH2:42]N(C)C.Cl.[C:47]1([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[C:49]([NH2:53])[CH:48]=1.CN([CH:63]=[O:64])C>CN(C1C=CN=CC=1)C.O>[C:47]1([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:52]=[CH:51][CH:50]=[C:49]([NH:53][C:63](=[O:64])[CH:41]([N:17]2[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:31])[F:32])[CH2:21][CH2:22]2)[CH:42]=[O:10])[CH:48]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 167173-AminobiphenylHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 86634607HCID 86634607, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (44 mg, 0.3 mmol) and DMAP (47 mg, 0.38 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (102 mg, 0.29 mmol) in DMF (5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (68 mg, 0.35 mmol) followed by biphenyl-3-yl-amine (55 mg, 0.32 mmol) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water and the product extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using silica gel 60-120 mesh using 70% ethyl acetate in hexane to afford 64 mg (44%) of N-biphenyl-3yl-3-oxo-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 496.18 (M+1)+, 98.7%. 1H NMR: (DMSO-d6): δ10.2 (d, 2H), 7.94-7.8 (dd, 2H), 7.8 (t, 1H), 7.7-7.52 (m, 5H), 7.52 (t, 2H), 7.42-7.32 (bs, 3H), 3.86-3.5 (m, 6H), 3.5-3.38 (m, 2H), 3.22 (d, 2H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a69b5cbd5aea47a78ee5b7980ad7c932
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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