Triethylamine → 8-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 517756Notes

Reaction equation

HRID 517756 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:6]=[N:5][N:4]=1.Cl.[C:19]1(=[O:29])[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][NH:20]1.C(N(CC)CC)C>C(#N)C>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([N:7]2[C:3]([CH2:2][N:26]3[CH2:27][CH2:28][C:23]4([C:19](=[O:29])[NH:20][CH2:21][CH2:22]4)[CH2:24][CH2:25]3)=[N:4][N:5]=[N:6]2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80271755-(Chloromethyl)-1-(3-(trifluoromethyl)phenyl)-1H-tetrazoleHCID 426145582,8-Diazaspiro(4.5)decan-1-one hydrochloride

Product 1

HCID 866918858-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole (200 mg, 0.762 mmol, commercially available from Otava, Kiev, Ukraine) in acetonitrile (4 mL) was added 2,8-diazaspiro[4.5]decan-1-one hydrochloride (290 mg, 1.52 mmol, Tyger Scientific, Ewing, USA) and triethylamine (0.318 mL, 2.29 mmol). The reaction mixture was heated at 120° C. for 20 minutes in a microwave reactor. The reaction mixture was then cooled and the solvent removed under vacuum. The residue was purified by MDAP. Fractions containing the desired product were combined and the solvent removed. The product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL) and the organic layer collected via a hydrophobic frit. The solvent was removed under a stream of argon to yield the title compound as a solid (0.161 g).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe solvent removed under vacuum
  3. customThe residue was purified by MDAP
  4. additionFractions containing the desired product
  5. customthe solvent removed
  6. customThe product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL)
  7. customthe organic layer collected via a hydrophobic frit
  8. customThe solvent was removed under a stream of argon

Sources & evidence

ORD record
ord-c8ee20792b434d7182d52478267d2934
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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