6-Chloro-N-methyl-3-pyridinemethanamine → iso-Propyl 4-acetoxy-3-[(6-chloropyrid-3-ylmethyl)amino]but-2-enecarboxylate

HRID 1797837Notes

Reaction equation

HRID 1797837 reaction equation
[C:1]([O:4][CH2:5][C:6]#[C:7][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])(=[O:3])[CH3:2].[Cl:15][C:16]1[N:21]=[CH:20][C:19]([CH2:22][NH:23]C)=[CH:18][CH:17]=1>O1CCCC1>[C:1]([O:4][CH2:5][C:6]([NH:23][CH2:22][C:19]1[CH:20]=[N:21][C:16]([Cl:15])=[CH:17][CH:18]=1)=[CH:7][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 86649326Iso-propyl 4-acetoxybut-2-ynecarboxylate

Product 1

HCID 86649325iso-Propyl 4-acetoxy-3-[(6-chloropyrid-3-ylmethyl)amino]but-2-enecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an initial charge of 124 mg (0.672 mmol) of iso-propyl 4-acetoxybut-2-ynecarboxylate in 5 ml of anhydrous tetrahydrofuran (THF) are added dropwise 116 mg (0.739 mmol) of 1-(6-chloropyridin-3-yl)-N-methylmethanamine, dissolved in 1 ml of anhydrous THF, at room temperature. The reaction mixture is stirred at room temperature for 16 h and concentrated under reduced pressure. Subsequently, the residue is taken up with toluene and washed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution. After drying over magnesium sulphate and concentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate are obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution
  3. dry with materialAfter drying over magnesium sulphate
  4. concentrationconcentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate
  5. customare obtained

Sources & evidence

ORD record
ord-a49d1405dfc24e3f89814c4ad6668d7b
Source dataset
uspto-grants-2013_01
Patent number
US08343893B2

Reaction notes

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