Pyridine → HCID 131730978, compound

HRID 2035514Notes

Reaction equation

HRID 2035514 reaction equation
[F:1][C:2]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:9]=[CH:8][C:7]=1[CH2:25][C:26]([NH2:28])=[O:27].N1C=CC=CC=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][N:22]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)[N:9]=[CH:8][C:7]=1[CH2:25][C:26]([NH2:28])=[O:27]

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 131730961HCID 131730961, compound

Product 1

HCID 131730978HCID 131730978, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 60 mg of 4-[(2,3-difluorobenzyl)amino]-6-([4-(piperazin-1-yl)phenyl]amino)pyridine-3-carboxyamide (the compound of Example 220) in 2 mL of methylene chloride, under ice cooling, 20 mg of pyridine and 28 mg of methanesulfonyl chloride were added, and stirred at room temperature for 30 minutes. To the reaction mixture, saturated sodium bicarbonate in water was added, extracted with chloroform:methanol (5:1), washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 47 mg (65%) of the title compound as a brown powder.

Workup

  1. extractionextracted with chloroform:methanol (5:1)
  2. washwashed 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:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-2ad4d2888ec34a8ca0eb6ebf4023517f
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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