1-Hydroxybenzotriazole → HCID 178523531, compound

HRID 1093607Notes

Reaction equation

HRID 1093607 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[Cl:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[S:58][CH:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1>CN(C=O)C.O>[Cl:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[S:58][CH:59]1[CH2:64][CH2:63][N:62]([C:16](=[O:18])[CH2:15][NH:14][C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][N:10]=2)=[O:13])[CH2:61][CH2:60]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 177498024-(2-Chlorophenylsulfanyl)piperidine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178523531HCID 178523531, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.04 g, 0.00014 mol) in DMF (1 mL) was added DIPEA (0.05517 g, 0.00043 mol), HOBt (0.023 g, 0.00017 mol) and EDCI.HCl (0.0326 g, 0.00017 mol) at ambient temperature. After 2 minutes 4-(2-chloro-phenylsulfanyl)-piperidine hydrochloride (0.0449 g, 0.00017 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried to afford 0.054 g (84%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-chlorophenylsulfanyl)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 455.12 (M+1)+, 83.96%, 1H NMR (DMSO-d6): δ 13.65 (s, 1H), 8.1 (s, 1H), 7.8 (d, 2H), 7.5 (m, 4H), 7.38 (t, 2H), 7.24 (t, 2H), 7.15 (s, 1H), 4.2 (m, 3H), 3.85 (m, 1H), 3.65 (m, 1H), 3.25 (m, 1H), 3.0 (m, 1H), 2.0 (m, 2H), 1.56 (m, 1H), 1.4 (m, 1H).

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-0b6bac6837e744aca877efe91a80765c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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