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Diisopropylethylamine → 2-Methyl-4-(1-m-tolyl-1H-[1,2,4]triazole-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 334076
Notes
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Reaction equation

HRID 334076 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[N:10][C:9]([C:12]([OH:14])=O)=[N:8]2)[CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH:55]1[CH3:60])=[O:53])([CH3:50])([CH3:49])[CH3:48]>C(Cl)Cl>[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][N:57]([C:12]([C:9]2[N:10]=[CH:11][N:7]([C:3]3[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=3)[N:8]=2)=[O:14])[CH2:56][CH:55]1[CH3:60])=[O:53])([CH3:50])([CH3:48])[CH3:49]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateHCID 713020901-(m-Tolyl)-1H-1,2,4-triazole-3-carboxylic acid

Product 1

HCID 866882982-Methyl-4-(1-m-tolyl-1H-[1,2,4]triazole-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.00 g (9.84 mmol) 1-m-tolyl-1H-[1,2,4]-triazole-3-carboxylic acid was stirred with 3.30 g (10.3 mmol) TBTU and 2.50 mL (14.6 mmol) DIPEA in 30 mL DCM at RT. After 10 min, 2.05 g (9.84 mmol) 2-methyl-piperazine-1-carboxylic acid tert-butyl ester was added and the reaction mixture was stirred at RT for 12 h. The solvent was removed by distillation. The residue was taken up in water and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc).

Workup

  1. customThe solvent was removed by distillation
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-06ba802c7e5647bfa4f310cb086af794
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883789B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes