Chloroacetic Acid → 2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide
Reaction equation
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[NH:16])=[CH:5][CH:4]=1.[Cl:17][CH2:18][C:19](O)=[O:20].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C>[Cl:17][CH2:18][C:19]([N:16]=[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]1[CH2:9][C:6]1[CH:7]=[N:8][C:3]([Cl:2])=[CH:4][CH:5]=1)=[O:20]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 82 mg (0.67 mmol) of DMAP, 25 mg (0.27 mmol) of chloroacetic acid and 62 mg (0.32 mmol) of EDC-HCl were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, dichloromethane was added thereto to dilute the mixture, and the mixture was washed with water and a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 4 mg (yield 5%).
Workup
- additionto dilute the mixture
- washthe mixture was washed with water
- dry with materiala 1% HCl aqueous solution, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto obtain the subject material
- customAmount obtained 4 mg (yield 5%)
Sources & evidence
- ORD record
- ord-f048738be80f43b3b36f4745a3feac78
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301525B2
Reaction notes
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