1,2-Dichloroethane → HCID 59525578, compound

HRID 385906Notes

Reaction equation

HRID 385906 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:12])[C:9]([O-])=[O:10])[CH:5]=[CH:4][CH:3]=1.[K+].C1C=CC2N(O)N=[N:20][C:18]=2C=1.C(Cl)CCl.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:12])[C:9]([NH:20][CH3:18])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 86646269HCID 86646269, compound

Product 1

HCID 59525578HCID 59525578, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium (6-bromopyridin-2-yl)(hydroxy)acetate (423 mg, 1.57 mmol), HOBT (600 mg, 3.91 mmol), EDC (750 mg, 3.91 mmol), and methylamine hydrochloride (529 mg, 7.83 mmol) were taken up in DMF (5.0 mL), and DIEA (684 μL, 3.91 mmol) was added. The reaction was stirred at room temperature for 6 hours, diluted with water, and extracted with 5:1 CH2Cl2:MeOH (2×). The combined organic layers were dried over MgSO4, filtered, and evaporated. Silica gel chromatography (40-100% EtOAc/hexanes) provided the title compound as a colorless solid.

Workup

  1. extractionextracted with 5:1 CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d2d9e480eec143ec965f4aab0017de3a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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