Triethylamine → HCID 58447051, compound

HRID 1045778Notes

Reaction equation

HRID 1045778 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([N:9]=[N:10][N:11]=2)[C:5](Cl)=[N:6][CH:7]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]2[N:4]([N:9]=[N:10][N:11]=2)[C:5]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 58447058HCID 58447058, compound

Product 1

HCID 58447051HCID 58447051, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

A 250 mL round bottom flask was charged with 8-bromo-5-chlorotetrazolo[1,5-c]pyrimidine (10 g, 42.7 mmol), tert-butyl piperazine-1-carboxylate (11.9 g, 64 mmol), triethylamine (13 g, 0.13 mol) and ethanol (200 mL). The resulting mixture was heated at 30° C. for 2 h under N2 and then cooled to room temperature. The mixture was concentrated under reduced pressure to dryness. The residue was diluted with water (20 mL) and extracted with dichloromethane (20 mL×3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated in vacuo, to afford 15.4 g (94%) of the product as an off-white solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated under reduced pressure to dryness
  3. additionThe residue was diluted with water (20 mL)
  4. extractionextracted with dichloromethane (20 mL×3)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-675c22fa3f1447298249b221403d11a7
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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