Pyridine → HCID 86606909, compound

HRID 2116773Notes

Reaction equation

HRID 2116773 reaction equation
[N:1]1([NH:7][C:8](=[O:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([OH:19])=O)=[C:11]([C:20]#[N:21])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN1CCOCC1.S(Cl)(Cl)=O.[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][N:36]=1.N1C=CC=CC=1>ClCCl>[N:1]1([NH:7][C:8](=[O:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][N:36]=3)=[O:19])=[C:11]([C:20]#[N:21])[CH:10]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 661742-Amino-5-chloropyridineHCID 86606908HCID 86606908, compound

Product 1

HCID 86606909HCID 86606909, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Cyano-4-carboxymethoxybenzoic acid (4-morpholinyl)amide (10 g, 0.0345 mol) is suspended in dichloromethane (50 ml), and thereto is added N-methylmorpholine (3.79 ml, 0.0345 mol) for dissolution. After adding thionyl chloride (2.8 ml, 0.0396 mol) under ice-cooling, the mixture is stirred at room temperature overnight. A solution of 2-amino-5-chloropyridine (4.87 g, 0.0379 mol) and pyridine (6.10 ml, 0.0758 mol) in methylene chloride (150 ml) is ice-cooled, and thereto is added dropwise the previously prepared acid chloride solution. After stirring at room temperature for 30 minutes, the reaction solution is washed with 10% hydrochloric acid, water, aqueous saturated sodium bicarbonate, and water, successively, dried over magnesium sulfate, and evaporated to remove the solvent to give 3-cyano-4-(5-chloropyridin-2-ylaminocarbonylmethoxy)benzoic acid (4-morpholinyl)amide (13.3 g, 96%).

Workup

  1. dissolutionfor dissolution
  2. temperaturecooling
  3. temperaturecooled
  4. stirringAfter stirring at room temperature for 30 minutes
  5. washthe reaction solution is washed with 10% hydrochloric acid, water, aqueous saturated sodium bicarbonate, and water
  6. dry with materialsuccessively, dried over magnesium sulfate
  7. customevaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-6842f153e7f74508af61b41c1ff85c10
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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