Dimethylformamide → HCID 58968646, compound

HRID 2075042Notes

Reaction equation

HRID 2075042 reaction equation
[Br:1][C:2]1[CH:29]=[C:28]([CH3:30])[C:27]([C:31]([F:34])([F:33])[F:32])=[CH:26][C:3]=1[CH2:4][N:5]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)[C:6]1[N:7]=[N:8][NH:9][N:10]=1.[C:35](=O)([O-])[O-].[Na+].[Na+].CN(C)C=O.S(OC)(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[CH:29]=[C:28]([CH3:30])[C:27]([C:31]([F:34])([F:32])[F:33])=[CH:26][C:3]=1[CH2:4][N:5]([CH2:11][C:12]1[CH:13]=[C:14]([C:22]([F:23])([F:24])[F:25])[CH:15]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:17]=1)[C:6]1[N:7]=[N:8][N:9]([CH3:35])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 58968655N-(2-bromo-4-methyl-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine

Product 1

HCID 58968646HCID 58968646, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2-bromo-4-methyl-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine (76 mg, 0.135 mmol) in anhydrous THF (5 mL) was added sodium carbonate (28 mg, 0.270 mmol) and N,N-dimethylformamide (1 mL) followed by dimethyl sulfate (34 mg. 0.270 mmol). The solution was heated to 70° C. for 18 hours then the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (20 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL) and the combined organics were washed with water (3×20 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (76 mg, 97.5%). 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H) 7.62 (s, 2H) 7.44(s, 1H) 7.40(s, 1H) 4.79(s, 2H) 4.76(s, 2H) 4.20(s, 3H) 2.39(s, 3H). LC-MS calc. 576 found 577 (M+H)

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (20 mL) and water (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. washthe combined organics were washed with water (3×20 mL)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-175c826b8b68407681bf5baab886e087
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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