1-Hydroxybenzotriazole → HCID 57874460, compound

HRID 1093688

Reaction equation

HRID 1093688 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:16])[CH2:12][C:13]([OH:15])=O)[CH2:7][CH2:6]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:43]1([C:49]2[N:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11](=[O:16])[CH2:12][C:13]([NH:55][C:52]2[CH:53]=[N:54][C:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:50][CH:51]=2)=[O:15])[CH2:9][CH2:10]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628776-Phenylpyridin-3-amineHCID 57874403HCID 57874403, compound

Product 1

HCID 57874460HCID 57874460, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.08 g, 0.00027 mole) in DMF (3 mL) was added DMAP (0.049 g, 0.00040 mole), HOBt (0.043 g, 0.00032 mole) and EDCI.HCl (0.06 g, 0.00032 mole). After 2 minutes 6-phenyl-pyridin-3-ylamine (0.055 g, 0.00032 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 ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.0642 g (53%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LC-MS purity: 450.15 (M+1)+, 99.25%, 1H NMR (DMSO-d6): δ 10.4 (s, 1H), 8.8 (s, 1H), 8.2 (dd, 1H), 8.1-8.0 (m, 2H), 8.0-7.9 (m, 1H), 7.5-7.2 (m, 6H), 7.0-6.9 (m, 1H), 4.8-4.7 (m, 1H), 3.8-3.7 (m, 2H), 3.7-3.6 (s, 2H), 3.6-3.5 (m, 2H), 2.1-1.5 (m, 4H).

Workup

  1. extractionthe product was extracted with ethyl acetate 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-29c0be9450ca46059b41a909b6b04a31
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Linked notes

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