Dichloromethane → HCID 11685836, compound

HRID 1911760Notes

Reaction equation

HRID 1911760 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:25]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:26][CH3:27])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][C:9]1[N:10]=[N:11][NH:12][N:13]=1.[OH-].[Na+].[CH2:45](Cl)Cl.S(OC)(OC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:38][C:37]([F:40])([F:39])[C:35]1[CH:34]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:41])[F:42])[CH:36]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:25]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:26][CH3:27])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][C:9]1[N:10]=[N:11][N:12]([CH3:45])[N:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 58689769HCID 58689769, compound

Product 1

HCID 11685836HCID 11685836, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a suspension of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-ylmethyl)-amino]-methyl}-quinolin-2-yl)-cyclopentylmethyl-ethyl-amine (0.25 g, 0.423 mmol) in water (4 mL) was added sodium hydroxide (0.033 g, 0.846 mmol), the resulting mixture was stirred for 15 min at RT, and then DCM (4 mL) was added. Dimethyl sulfate (0.058 g, 0.465 mmol) was then added to this mixture, followed by tetrabutylammonium bromide (0.006 g, 0.021 mmol), and stirring of the resulting mixture was continued for 15 min. The organic layer was then separated from aqueous layer, the aqueous layer was extracted with DCM (3×10 mL), and the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum to afford a residue. This residue was purified by column chromatography over 100-200 mesh silica gel using 4% ethyl acetate in petroleum ether, to give the title compound (0.08 g, yield: 31.3%).

Workup

  1. stirringstirring of the resulting mixture
  2. waitwas continued for 15 min
  3. customThe organic layer was then separated from aqueous layer
  4. extractionthe aqueous layer was extracted with DCM (3×10 mL)
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto afford a residue
  9. customThis residue was purified by column chromatography over 100-200 mesh silica gel using 4% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d8dc7c6430b443f9b0fe345b1dc90726
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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