1-Hydroxybenzotriazole → HCID 178523529, compound

HRID 1093615Notes

Reaction equation

HRID 1093615 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.[Br: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>[Br: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 66591387HCID 66591387, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178523529HCID 178523529, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.15 g, 0.000533 mol) in DMF (3 mL) was added DIPEA (0.206 g, 0.00160 mol), HOBt (0.0864 g, 0.00064 mol) and EDCI.HCl (0.122 g, 0.00064 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenylsulfanyl)-piperidine hydrochloride (0.197 g, 0.00064 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. Purification by column chromatography using silica gel 60-120 mesh (40% ethyl acetate in hexane) afforded 0.097 g (36%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-phenylsulfanyl)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 499.07 (M+1)+, 95.7%, 1H NMR (DMSO-d6): δ 13.8 (d, 1H), 8.1 (t, 1H), 7.8 (d, 2H), 7.6 (dd, 1H), 7.58-7.3 (m, 6H), 7.22-7.06 (m, 2H), 4.3-4.1 (m, 3H), 3.9-3.6 (m, 2H), 3.0 (m, 1H), 2.0 (m, 2H), 1.7-1.4 (m, 3H).

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-09123555e2e74e9e91ca0fe23a9bbaf3
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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