Pyridine → HCID 178505024, compound

HRID 2205074Notes

Reaction equation

HRID 2205074 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8]/[C:9](/[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])=[N:10]\[C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:41](Cl)([CH3:44])(=[O:43])=[O:42]>ClCCl>[CH3:44][S:41]([NH:1][C:2]1[N:7]=[C:6]([NH:8]/[C:9](/[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:32])[F:33])=[N:10]\[C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 178507624HCID 178507624, compound

Product 1

HCID 178505024HCID 178505024, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-N-(((6-Aminopyridin-2-yl)amino)((2-(trifluoromethyl)benzyl)amino) methylene)-4-(trifluoromethyl)benzamide (200 mg, 0.42 mmol) was dissolved in dichloromethane (3.8 mL) and pyridine (0.4 mL) was added followed by mesyl chloride (32 μL, 0.42 mmol). The reaction was stirred at room temperature for 3 days, and another equivalent of mesyl chloride (32 μL, 0.42 mmol) was added, and stirring continued for another 24 h. The crude material then was concentrated, and the residue was partitioned between water and ethyl acetate, and the organic layer was washed with brine, then dried over sodium sulfate, and concentrated in vacuo to provide the crude product. The crude product was purified by chromatography (gradient: 8:2 hexanes:EtOAc to 2:8 hexanes:EtOAc) to provide the title compound (95 mg, 41% yield).

Workup

  1. stirringstirring
  2. waitcontinued for another 24 h
  3. concentrationThe crude material then was concentrated
  4. customthe residue was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto provide the crude product
  9. customThe crude product was purified by chromatography (gradient: 8:2 hexanes:EtOAc to 2:8 hexanes:EtOAc)

Sources & evidence

ORD record
ord-6a1f0317a9f7409b9f20a3122d1952cc
Source dataset
uspto-grants-2016_06
Patent number
US09370507B2

Reaction notes

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