Triethylamine → tert-butyl (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetate

HRID 729455Notes

Reaction equation

HRID 729455 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[N:15][C:14]([C:17]3[N:18]=[N:19][NH:20][N:21]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>C1COCC1>[Br:1][C:2]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]3[N:18]=[N:19][N:20]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[N:21]=3)=[N:15][CH:16]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 57832734HCID 57832734, compound

Product 1

HCID 86621799tert-butyl (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-5-(2H-tetrazol-5-yl)pyrazine from Step 6 (5.00 g, 11.9 mmol) and triethylamine (3.32 mL, 23.8 mmol) in THF (50 mL) at 60° C. was added tert-butyl bromoacetate (3.48 g, 17.9 mmol). After a period of 1 h at 60° C., the reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic phase was separated, dried over sodium sulfate, filtered and evaporated. To the solid was added 50 mL of acetone followed by slow addition of 100 mL of hexane. The resulting solid was filtered to provide tert-butyl (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetate.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. additionTo the solid was added 50 mL of acetone
  7. additionfollowed by slow addition of 100 mL of hexane
  8. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-9412a985543a4603a570e372dbcb6613
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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