1-Hydroxybenzotriazole → HCID 57874431, compound

HRID 1093672Notes

Reaction equation

HRID 1093672 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH:29]1[CH:30]=[CH:31]C2N(O)N=[N:35][C:33]=2[CH:34]=1.CCN=C=NCCCN(C)C.Cl.Cl.[N+:52]([C:55]1[CH:67]=[CH:66][CH:65]=[CH:64][C:56]=1[O:57]N1CCCCC1)([O-:54])=[O:53]>CN(C=O)C.O>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([N:35]2[CH2:31][CH2:30][CH:29]([O:57][C:56]3[CH:64]=[CH:65][CH:66]=[CH:67][C:55]=3[N+:52]([O-:54])=[O:53])[CH2:34][CH2:33]2)=[O:12])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55049154N-biphenyl-4-yl-malonamic acidHCID 66591597HCID 66591597, compound

Product 1

HCID 57874431HCID 57874431, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-biphenyl-4-yl-malonamic acid (0.1 g, 0.00039 mole) in DMF (3 mL) was added DIPEA (0.176 g, 0.0014 mole), HOBt (0.078 g, 0.00058 mole) and EDCI.HCl (0.11 g, 0.00058 mole). After 2 minutes (2-nitro-phenoxy)-piperidine hydrochloride (0.12 g, 0.00046 mole) and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using neutral aluminium oxide (5% methanol in chloroform) to afford 0.130 g (72%) of N-biphenyl-4-yl-3-[4-(2-nitro-phenoxy)-piperidin-1-yl]-3-oxo-propionamide. LC-MS purity: 460.18 (M+1)+, 95%, 1H NMR (DMSO-d6): δ 7.9 (m, 1H), 7.7 (m, 7H), 7.5 (m, 3H), 7.3 (m, 1H), 7.1 (m, 1H), 5.0 (m, 1H), 3.6 (m, 6H), 2.0 (m, 2H), 1.8 (m, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d86e0d18c2d74946b45f02006762340b
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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