1-Hydroxybenzotriazole → HCID 178523515, compound

HRID 1093738Notes

Reaction equation

HRID 1093738 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[Cl:51][C:52]1[CH:53]=[C:54]([CH:62]=[CH:63][CH:64]=1)[O:55][CH:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>CN(C=O)C.O>[Cl:51][C:52]1[CH:53]=[C:54]([CH:62]=[CH:63][CH:64]=1)[O:55][CH:56]1[CH2:57][CH2:58][N:59]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]2[CH:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:20][N:19]=2)=[O:22])[CH2:60][CH2:61]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353164-(3-Chlorophenoxy)piperidine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178523515HCID 178523515, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (155 mg, 1.2 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (99 mg, 0.4 mmol) in DMF (2 mL) followed by HOBt (54 mg, 0.4 mmol) and EDCI.HCl (84 mg, 0.44 mmol). After 2 minutes 4-(3-chloro-phenoxy)-piperidine hydrochloride (100 mg, 0.4 mmol) (prepared by method used for the synthesis of Intermediate 15) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by washing with methanol to afford 67 mg (39.4% Yield) 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(3-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 439, 92.8%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.0 (m, 1H), 7.8 (m, 2H), 7.5 (m, 2H), 7.4 (m, 1H), 7.3 (m, 2H), 7.1 (m, 2H), 7.0 (m, 2H), 4.7 (m, 1H), 4.2 (m, 2H), 4.0 (m, 1H), 3.7 (m, 1H), 3.4 (m, 1H), 3.2 (m, 1H), 2.0 (m, 2H), 1.5 (m, 2H).

Workup

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure The residue
  5. customwas purified
  6. washby washing with methanol

Sources & evidence

ORD record
ord-40d65119483b4ec0883783cf42478ffc
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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