Pyridine → HCID 131730969, compound

HRID 2035506Notes

Reaction equation

HRID 2035506 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[CH:21][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[C:19]([NH:27][CH2:28][C:29]4[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=4)[CH:18]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.N1C=CC=CC=1.[CH3:43][S:44](Cl)(=[O:46])=[O:45].O.N>C(Cl)(Cl)Cl>[F:36][C:31]1[CH:30]=[C:29]([CH:34]=[C:33]([F:35])[CH:32]=1)[CH2:28][NH:27][C:19]1[CH:18]=[C:17]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][S:44]([CH3:43])(=[O:46])=[O:45])[CH2:5][CH2:6]3)=[CH:11][CH:12]=2)[N:22]=[CH:21][C:20]=1[CH2:23][C:24]([NH2:26])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12896473Azane;hydrateHCID 131730968HCID 131730968, compound2×

Product 1

HCID 131730969HCID 131730969, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

60 mg of 6-({4-[4-(2-aminoethyl)piperazin-1-yl]phenyl}amino)-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 248) was suspended in 6 mL of chloroform, to which, under ice cooling, 20 mg of pyridine and 17 mg of methanesulfonyl chloride were added, and stirred at the same temperature for 20 minutes. To the reaction mixture, ammonia water was added, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1), recrystallized from chloroform-methanol-ether to obtain 40 mg (57%) of the title compound as a slight yellow crystalline powder.

Workup

  1. extractionextracted with chloroform
  2. washthe extract was washed with saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1)
  6. customrecrystallized from chloroform-methanol-ether

Sources & evidence

ORD record
ord-92fafa26e51345819cf3fdf07141d072
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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