Triethylamine → HCID 131730935, compound

HRID 2035485Notes

Reaction equation

HRID 2035485 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:31][C:32]([NH2:34])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44].C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][CH:25]([CH2:28][CH2:29][O:30][S:43]([CH3:42])(=[O:45])=[O:44])[CH2:26][CH2:27]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:31][C:32]([NH2:34])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 131730936HCID 131730936, compound

Product 1

HCID 131730935HCID 131730935, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

60 mg of 4-(benzylamino)-6-({4-[4-(2-hydroxyethyl)piperidin-1-yl]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 57), 18 mg of triethylamine and 2 mg of 4-dimethylaminopyridine were dissolved in 5 mL of tetrahydrofuran, to which 18 mg of methanesulfonyl chloride was added under ice cooling, and stirred at the same temperature for 2 hours. Saturated aqueous sodium bicarbonate was added to the reaction mixture, extracted with chloroform, the extract was washed with water, 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) to obtain 44 mg (62%) of the title compound as a light brown crystalline powder.

Workup

  1. additionwas added under ice cooling
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-1566fcf693124047b31294921c639205
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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