Formaldehyde → 1-(4-Chlorophenyl)-5-[(3,3-difluoro-1-pyrrolidinyl)methyl]-1H-tetrazole

HRID 517761

Reaction equation

HRID 517761 reaction equation
Cl.[F:2][C:3]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4]1.C=O.C([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.[Cl:18][C:19]1[CH:24]=CC([N+]#[C-])=[CH:21][CH:20]=1.C[Si]([N:31]=[N+:32]=[N-:33])(C)C>CO>[Cl:18][C:19]1[CH:24]=[CH:17][C:16]([N:13]2[C:14]([CH2:15][N:5]3[CH2:6][CH2:7][C:3]([F:8])([F:2])[CH2:4]3)=[N:33][N:32]=[N:31]2)=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 746704-Chlorophenyl isocyanideHCID 78378AzidotrimethylsilaneHCID 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 680745081-(4-Chlorophenyl)-5-[(3,3-difluoro-1-pyrrolidinyl)methyl]-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,3-difluoropyrrolidine hydrochloride (129 mg, 0.90 mmol, Sigma-Aldrich) in methanol (3 mL) was added formaldehyde (37% aqueous) (0.067 mL, 0.90 mmol) and triethylamine (0.139 mL, 1.00 mmol). The reaction mixture was shaken at room temperature for 2 hours. To the reaction mixture was added 4-chlorophenyl isocyanide (138 mg, 1.00 mmol) and trimethylsilylazide (0.133 mL, 1.00 mmol). The reaction mixture was shaken at room temperature for a further 18 hours.

Workup

  1. stirringThe reaction mixture was shaken at room temperature for a further 18 hours

Sources & evidence

ORD record
ord-cd43199020bd453d94a2a1123bc5b8fa
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Linked notes

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