tert-butyl (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetate → HCID 24970224, compound

HRID 729457Notes

Reaction equation

HRID 729457 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][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]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[N:21]=3)=[N:15][CH:16]=2)[CH2:7][CH2:6]1>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][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]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=3)=[N:15][CH:16]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 1

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

Product 1

HCID 24970224HCID 24970224, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetate (2.50 g, 4.68 mmol) was dissolved in a mixture of TFA (11.3 mL) and water (1.3 mL). After a period of 18 h at room temperature the reaction mixture was evaporated followed by two co-evaporations with toluene. The yellow oil was dissolved in ethyl acetate (12.5 mL) and hexane (37.5 mL) was then added slowly. The resulting solid was filtered to provide (5-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazin-2-yl}-2H-tetrazol-2-yl)acetic acid.

Workup

  1. customAfter a period of 18 h at room temperature the reaction mixture was evaporated
  2. dissolutionThe yellow oil was dissolved in ethyl acetate (12.5 mL)
  3. additionhexane (37.5 mL) was then added slowly
  4. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-cd6021ce4ad74ec1a37df22a21b314b4
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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