Dimethylformamide → HCID 131722786, compound

HRID 1386517Notes

Reaction equation

HRID 1386517 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:16]([CH3:18])[CH3:17])([CH2:12][CH2:13][CH2:14][Cl:15])[C:10]#[N:11])=[CH:5][CH:4]=1.CN[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:36][N:37](C=O)[CH3:38]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[ClH:15].[CH3:17][CH:16]([C:9]([CH2:12][CH2:13][CH2:14][N:37]([CH3:38])[CH2:36][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:19])[F:1])=[CH:4][CH:5]=1)[C:10]#[N:11])[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 21181453HCID 21181453, compound

Product 1

HCID 131722786HCID 131722786, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

A mixture of the product of Example 7, Step (b) (271 mg, 0.89 mmole), methyl benzylamine (2.42 mg, 2.00 inmoles), tetra-n-butylammonium iodide (37 mg, 10 mmole %), and anhydrous potassium carbonate (2.76 mg, 2.00 mmoles) in 1.0 mL DMF was stirred overnight at 80-86°. After cooling, the mixture was partitioned between diethyl ether and water. The aqueous layer was extracted with ether, the combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated. Chromatography of the residue over silica gel using 20% ethyl acetate-hexane as eluent gave the title compound as the free base. A methanol solution of the free base was acidified with a solution of hydrochloric chloride in methanol, the solvent evaporated, and the residue crystallized from ethyl acetate-hexane to give a product compound (53 mg) as a white crystalline solid, characterized as follows: Analysis for C23H28ClF3N2•¼ H2O (mw 429.44): Calculated: C, 64.35; H, 6.69; N, 6.52; Found: C, 64.60; H, 6.70; N, 6.52.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between diethyl ether and water
  3. extractionThe aqueous layer was extracted with ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-0d57c15c0ff548f09b0c0e6bf94f332f
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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