1-Hydroxybenzotriazole → HCID 66577664, compound

HRID 1183262Notes

Reaction equation

HRID 1183262 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([N:27]2[CH2:28][CH2:29][N:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:17])[CH2:25][CH2:26]2)=[O:16])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 919652-MeppHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 66577664HCID 66577664, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (0.100 g, 0.35 mmol), 1-(2-methylphenyl)piperazine (0.092 g, 0.52 mmol), and 1-hydroxybenzotriazole (0.096 g, 0.71 mmol) in 5:1 CH2Cl2:DMF was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.136 g, 0.71 mmol), and the reaction was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and washed twice with H2O, once with brine, and then dried over Na2SO4, filtered, and concentrated to give the title compound, which was used directly in the following step.

Workup

  1. washwashed twice with H2O, once with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-564745f8b37e433abc728acb5f4b06e5
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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