Dichloromethane → HCID 58689761, compound

HRID 1911768Notes

Reaction equation

HRID 1911768 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:13][C:14]1[C:15]([N:22]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[CH2:23][CH:24]2[CH2:26][CH2:25]2)=[N:16][C:17]([CH3:21])=[C:18]([CH3:20])[CH:19]=1)[C:8]1[N:9]=[N:10][NH:11][N:12]=1.[OH-].[Na+].[CH2:42](Cl)Cl.S(OC)(OC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:39][C:2]([F:38])([F:1])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:13][C:14]1[C:15]([N:22]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[CH2:27][CH:28]2[CH2:30][CH2:29]2)=[N:16][C:17]([CH3:21])=[C:18]([CH3:20])[CH:19]=1)[C:8]1[N:9]=[N:10][N:11]([CH3:42])[N:12]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 58689781HCID 58689781, compound

Product 1

HCID 58689761HCID 58689761, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a suspension of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-methyl}-5,6-dimethyl-pyridin-2-yl)-bis-cyclopropylmethyl-amine (0.3 g, 0.54 mmol), obtained in step (viii), in water (4 mL) was added sodium hydroxide (0.04 g, 1.0 mmol), and this mixture was stirred for 15 min at RT, followed by the addition of DCM (4 mL). Dimethyl sulfate (0.13 g, 1.03 mmol) was then added to this mixture, followed by the addition of tetrabutylammonium bromide (0.008 g, 0.024 mmol). The mixture was then stirred for 0.5 h, after which the organic layer was separated from the aqueous layer which was extracted with DCM (3×10 mL). The combined organic layer was washed with brine, dried over sodium sulfate, and then concentrated under vacuum to afford the title compound as light yellow oil (0.200 g, yield: 66.6%).

Workup

  1. stirringThe mixture was then stirred for 0.5 h
  2. customafter which the organic layer was separated from the aqueous layer which
  3. extractionwas extracted with DCM (3×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4f74fb807e34917bec7dd7d7eda8dd9
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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