1-Hydroxybenzotriazole → HCID 44231444, compound

HRID 1665646Notes

Reaction equation

HRID 1665646 reaction equation
C1C=CC2N(O)N=NC=2C=1.[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[CH2:19][CH2:18]1)[CH2:13][C:14](O)=[O:15].CCN=C=NCCCN(C)C.Cl.[C:46]1([C:52]2[N:57]=[CH:56][C:55]([NH2:58])=[CH:54][CH:53]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:25]=[C:26]([F:32])[C:27]([F:31])=[C:28]([F:30])[CH:29]=2)[CH2:19][CH2:18]1)[CH2:13][C:14]([NH:58][C:55]1[CH:56]=[N:57][C:52]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:53][CH:54]=1)=[O:15]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628776-Phenylpyridin-3-amineHCID 57875813HCID 57875813, compound

Product 1

HCID 44231444HCID 44231444, compoundYield 36.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (40 mg, 0.3 mmol) and DMAP (46 mg, 0.37 mmol) were added to a stirred solution of 3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionic acid (83 mg, 0.25 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (58 mg, 0.3 mmol) followed by 6-phenyl-pyridin-3-ylamine (51 mg, 0.3 mmol) were added. The reaction mixture was stirred at room temperature overnight, diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 44 mg (36%) of 3-oxo-N-(6-phenyl-pyridin-3-yl)-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 483.16 (M+1)+, 97.0%, 1H NMR: (DMSO-d6): δ 10.5 (s, 1H), 8.8 (d, 1H), 8.2-8.1 (m, 1H), 8.1 (d, 2H), 8.0 (d, 1H), 7.6-7.4 (m, 5H), 3.4-3.2 (m. 10H).

Workup

  1. additionwere added
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8fc3171d61f4680bac49d83b8d8ed99
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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