1-Hydroxybenzotriazole → tert-Butyl 4-(4-(3-phenylureido)benzoyl)piperazine-1-carboxylate

HRID 1878401Notes

Reaction equation

HRID 1878401 reaction equation
[C:1]1([NH:7][C:8](=[O:19])[NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(#N)C>[C:1]1([NH:7][C:8](=[O:19])[NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:23]3[CH2:22][CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24]3)=[O:16])=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2312784-[(Phenylcarbamoyl)amino]benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 46511620tert-Butyl 4-(4-(3-phenylureido)benzoyl)piperazine-1-carboxylateYield 67.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-phenylureido)benzoic acid (13.5 g, 52.68 mmol) in acetonitrile (250 mL) at room temperature was added tert-butyl piperazine-1-carboxylate (11.8 g, 63.22 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (21.1 g, 156.5 mmol, HOBT) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (30 g, 156.5 mmol, EDCl). The mixture was stirred at reflux temperature for 16 hours and was then concentrated under vacuum. The residue was submitted to silica chromatography (0-5% ethyl acetate in n-hexanes as eluant) to give the title compound (15.0 g). MS (ESI) m/z 425.1 [M+H]+

Workup

  1. temperatureat reflux temperature for 16 hours
  2. concentrationwas then concentrated under vacuum

Sources & evidence

ORD record
ord-9979c530d824497f9bec58142a923e92
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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