Formaldehyde → 1,1-Dimethylethyl 2-methyl-4-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-1-piperazinecarboxylate

HRID 517706Notes

Reaction equation

HRID 517706 reaction equation
[CH2:1]=O.[CH3:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:24]=[CH:23][C:22]([N+:25]#[C-:26])=[CH:21][CH:20]=1.C[Si]([N:33]=[N+:34]=[N-:35])(C)C>CO>[CH3:3][CH:4]1[CH2:9][N:8]([CH2:1][C:26]2[N:25]([C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:27])([F:28])[F:17])=[CH:24][CH:23]=3)[N:35]=[N:34][N:33]=2)[CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanideHCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylate

Product 1

HCID 866918701,1-Dimethylethyl 2-methyl-4-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of formaldehyde (0.044 mL, 0.584 mmol) in methanol (2 mL) was added 1,1-dimethylethyl 2-methyl-1-piperazinecarboxylate (117 mg, 0.584 mmol). The reaction mixture was stirred at room temperature for 1 hour before the addition of 4-(trifluoromethyl)phenylisocyanide (100 mg, 0.584 mmol) and trimethylsilyl azide (0.092 mL, 0.701 mmol). The resulting reaction mixture was stirred at room temperature overnight.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-0ddb382cdc62441884a939f029b2d447
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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