1-Hydroxybenzotriazole → HCID 57874518, compound

HRID 1093696Notes

Reaction equation

HRID 1093696 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[CH2:15][C:16]([OH:18])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[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.[F:52][C:53]([F:69])([F:68])[C:54]1[CH:67]=[CH:66][CH:65]=[CH:64][C:55]=1[O:56]NC1CCNCC1>CN(C=O)C.O>[O:18]=[C:16]([N:35]1[CH2:31][CH2:30][CH:29]([O:56][C:55]2[CH:64]=[CH:65][CH:66]=[CH:67][C:54]=2[C:53]([F:52])([F:68])[F:69])[CH2:34][CH2:33]1)[CH2:15][C:14]([NH:13][C:10]1[CH:11]=[N:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH:9]=1)=[O:19]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874490N-(6-phenyl-pyridin-3-yl)-malonamic acidHCID 86634624HCID 86634624, compound

Product 1

HCID 57874518HCID 57874518, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(6-phenyl-pyridin-3-yl)-malonamic acid (0.07 g, 0.00024 mole) in DMF (1 mL) was added DIPEA (0.153 g, 0.00120 mole), HOBt (0.039 g, 0.00029 mole) and EDCI.HCl (0.055 g, 0.00029 mole). After 2 minutes (2-trifluoromethyl-phenoxy)-piperidin-4-yl-amine hydrochloride (0.080 g, 0.00029 mole) was added 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 layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 57.5 mg (50%) of 3-oxo-N-(6-phenyl-pyridin-3-yl)-3-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-propionamide. LC-MS purity: 484.18 (M+1)+, 98.83%, 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.8 (d, 1H), 8.2 (d, 1H), 8.1 (d, 2H), 8.0 (d, 1H), 7.7-7.6 (m, 2H), 7.5-7.3 (m, 4H), 7.1 (t, 1H), 4.9 (m, 1H), 3.7-3.5 (m, 6H), 2.0-1.6 (m, 4H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27752f1ab35f4ffb904323257f5227b5
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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