1,2-Dichloroethane → 2-Morpholin-4-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 2282449Notes

Reaction equation

HRID 2282449 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[N:10]1([CH:16]([CH3:20])[C:17](O)=[O:18])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>C(Cl)Cl.[Cl-].[Na+].O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:17](=[O:18])[CH:16]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH3:20])=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 31525652-Morpholin-4-ylpropanoic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 866870312-Morpholin-4-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazideYield 99.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (1.62 g, 12.8 mmol), 2-(morpholin-4-yl)propanoic acid (Enamine, 2.50 g, 12.8 mmol), HOBt.H2O (196 mg, 1.28 mmol) and Et3N (2.14 mL, 15.3 mmol) in DCM (50 mL) was added EDC (2.94 g, 15.3 mmol) and the brown solution stirred at RT for 16 h. Water (20 mL) and brine (20 mL) were added, and the mixture shaken. The aqueous layer was extracted with DCM (20 mL), then the combined organics were passed through a hydrophobic frit and concentrated in vacuo to give the title compound as a brown foam (3.43 g, >99%). LCMS (Method 3): Rt 0.44 min, m/z 269 [MH+].

Workup

  1. stirringthe mixture shaken
  2. extractionThe aqueous layer was extracted with DCM (20 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-133ae318a96647efaea020bf4121eda5
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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