1,2-Dichloroethane → HCID 59525654, compound

HRID 385955Notes

Reaction equation

HRID 385955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([C:15]([O-:17])=O)=[CH:4][CH:3]=1.[Na+].C(Cl)CCl.C1C=CC2N(O)N=[N:29]C=2C=1.[Cl-].[NH4+].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([C:15]([NH2:29])=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 111,2-Dichloroethane2×HCID 25517Ammonium Chloride2×HCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 86646274HCID 86646274, compound

Product 1

HCID 59525654HCID 59525654, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium 6-chloro-2-(morpholin-4-ylmethyl)pyridine-3-carboxylate (0.3 g, 1.077 mmol), EDC (0.619 g, 3.23 mmol), HOBt (0.495 g, 3.23 mmol), ammonium chloride (0.173 g, 3.23 mmol) and DIPEA (1.128 mL, 6.46 mmol) were stirred in DMF (10 mL) at room temperature overnight. Additional EDC (0.619 g, 3.23 mmol), HOBt (0.495 g, 3.23 mmol), ammonium chloride (0.173 g, 3.23 mmol) and DIPEA (1.128 mL, 6.46 mmol) were then added and stirring continued at room temperature for 24 hours. Saturated aqueous NaHCO3 was added and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a yellow solid.

Workup

  1. extractionthe products were extracted into EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9088a3b1b444cc79804d00adc9ba86b
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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