2,6-Diaminopyridine → HCID 178507624, compound

HRID 2205073Notes

Reaction equation

HRID 2205073 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10](=S)[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[O:8])=[CH:5][CH:4]=1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[N:30]=1>CN(C=O)C.C(OCC)(=O)C>[NH2:28][C:29]1[N:30]=[C:31]([NH:35]/[C:10](/[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:9]\[C:7](=[O:8])[C:6]2[CH:24]=[CH:25][C:3]([C:2]([F:27])([F:26])[F:1])=[CH:4][CH:5]=2)[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 88612,6-DiaminopyridineHCID 86710863HCID 86710863, compound

Product 1

HCID 178507624HCID 178507624, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(trifluoromethyl)-N-((2-(trifluoromethyl)benzyl)carbamothioyl) benzamide (2.0 g, 4.92 mmol), 2,6-diaminopyridine (591 mg, 5.41 mmol), and 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC hydrochloride) (1.13 g, 5.91 mmol) in DMF (49 mL) was heated to 65° C. for 30 minutes, then allowed to cool to room temperature. The mixture was then diluted with ethyl acetate, washed with aqueous sodium bicarbonate solution, washed with brine, dried over sodium sulfate, and concentrated to provide the crude product. The crude product was purified by chromatography (gradient: 9:1 hexanes:EtOAc to 6:4 hexanes:EtOAc) to provide (Z)-N-(((6-aminopyridin-2-yl)amino)((2-(trifluoromethyl) benzyl)amino)methylene)-4-(trifluoromethyl)benzamide as a yellow solid (1.31 g, 55% yield).

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto provide the crude product
  6. customThe crude product was purified by chromatography (gradient: 9:1 hexanes:EtOAc to 6:4 hexanes:EtOAc)

Sources & evidence

ORD record
ord-8aff1afd29c649f98a62b735b6210ae9
Source dataset
uspto-grants-2016_06
Patent number
US09370507B2

Reaction notes

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