1,2-Dichloroethane → HCID 59526361, compound

HRID 385902Notes

Reaction equation

HRID 385902 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]([O-:11])=O)[CH:5]=[CH:4][CH:3]=1.[K+].C1C=CC2N(O)N=[N:25][C:23]=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]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]([NH:25][CH3:23])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 86646268HCID 86646268, compound

Product 1

HCID 59526361HCID 59526361, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium (6-bromopyridin-2-yl)(morpholin-4-yl)acetate (533 mg, 1.57 mmol), HOBT (361 mg, 2.36 mmol), EDC (452 mg, 2.36 mmol), and methylamine hydrochloride (318 mg, 4.71 mmol) were taken up in DMF (5.0 mL) and DIEA (0.41 mL, 2.36 mmol) was added. The reaction was maintained at room temperature overnight, then 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 (0-10% MeOH/CH2Cl2) yielded 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-904f85845e764cf19773dd480bdaf2b8
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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