3,4-dihydro-2H-pyran → HCID 57861278, compound

HRID 1960023Notes

Reaction equation

HRID 1960023 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[CH2:6][NH:7][C:8]1[N:9]=[N:10][N:11]([CH2:13][CH2:14][OH:15])[N:12]=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[F:20][C:19]([F:21])([F:22])[C:17]1[CH:16]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:18]=1)[CH2:6][NH:7][C:8]1[N:9]=[N:10][N:11]([CH2:13][CH2:14][O:15][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][O:25]2)[N:12]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57861289HCID 57861289, compound

Product 1

HCID 57861278HCID 57861278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(5-{N-[3,5-bis(trifluoromethyl)benzyl]amino}tetrazol-2-yl)ethanol (0.68 g, 1.9 mmol), 3,4-dihydro-2H-pyran (DHP, 0.35 g, 4.2 mmol) and a catalytic amount of pyridinium p-toluene sulfonate (PPTS, 0.050 g, 0.20 mmol) in CH2Cl2 (10 mL) is stirred at room temperature for 10 hours. The resulting mixture is quenched by addition of sat. NaHCO3 aq. and extracted with EtOAc. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give N-[3,5-bis(trifluoromethyl)benzyl]-N-{2-[2-(tetrahydropyran-2-yloxy)ethyl]-2H-tetrazol-5-yl}amine.

Workup

  1. customThe resulting mixture is quenched by addition of sat. NaHCO3 aq.
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-62db9daf2e0545dd90229b982fad898c
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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