1-Hydroxybenzotriazole → HCID 178424342, compound

HRID 1093616Notes

Reaction equation

HRID 1093616 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.[NH:52]1[CH2:57][CH2:56][CH:55]([NH:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[CH3:65])[CH2:54][CH2:53]1>CN(C=O)C.O>[O:18]=[C:16]([N:52]1[CH2:57][CH2:56][CH:55]([NH:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[CH3:65])[CH2:54][CH2:53]1)[CH2:15][NH:14][C:12]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][N:10]=1)=[O:13]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66545677Piperidin-4-yl-o-tolyl-amine dihydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178424342HCID 178424342, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.102 g, 0.00042 mol) in DMF (1 mL) was added DIPEA (0.245 g, 0.00190 mol), HOBt (0.056 g, 0.000418 mol) and EDCI.HCl (0.145 g, 0.00076 mol) at ambient temperature. After 2 minutes piperidin-4-yl-o-tolyl-amine dihydrochloride (0.1 g, 0.00038 mol) was added and the resulting mixture was stirred for 16 hours. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried to afford 0.15 g (94% of 5-phenyl-1H-pyrazole-3-carboxylic acid [2-oxo-2-(4-o-tolylamino-piperidin-1-yl)-ethyl]-amide.

Workup

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

Sources & evidence

ORD record
ord-568cf6567e3c4a389d9666d6ddb4b936
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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