Sodium Azide → 4-(2-Bromo-5-fluorophenoxy)-1-[5-(2H-tetrazol-5-yl)-1,3,4-thiadiazol-2-yl]piperidine

HRID 561197Notes

Reaction equation

HRID 561197 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[S:15][C:14]([C:16]#[N:17])=[N:13][N:12]=2)[CH2:7][CH2:6]1.[N-:23]=[N+:24]=[N-:25].[Na+].Cl.[NH+]1C=CC=CC=1.CO.CCOCC.CCCCCCC>CN1C(=O)CCC1>[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[S:15][C:14]([C:16]3[N:23]=[N:24][NH:25][N:17]=3)=[N:13][N:12]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 21584435Pyridinium hydrochlorideHCID 533885275-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazole-2-carbonitrileHCID 86620456MeOH Et2O heptane

Product 1

HCID 533883664-(2-Bromo-5-fluorophenoxy)-1-[5-(2H-tetrazol-5-yl)-1,3,4-thiadiazol-2-yl]piperidine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound was prepared in a similar manner as described in Example 1, Step 3, with 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazole-2-carbonitrile (15.6 g), NaN3 (13.2 g, 204 mmol) and pyridinium hydrochloride (9.47 g, 82.0 mmol) in NMP (70 mL), and purification by trituration with a mixture of MeOH/Et2O/heptane to afford the desired product as a white solid.

Workup

  1. customThe title compound was prepared in a similar manner

Sources & evidence

ORD record
ord-a8aeeea80efa4a19b1daaa5a422565ac
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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