Sodium hydride → HCID 59301401, compound

HRID 2236203Notes

Reaction equation

HRID 2236203 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.[H-].[Na+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C1COCC1.CN(C=O)C.CCOC(C)=O>[C:22]([O:21][C:19](=[O:20])[CH2:18][O:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 1176762-(N-Methyl-N-(5-nitro-2-pyridyl)amino)ethanol

Product 1

HCID 59301401HCID 59301401, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Hydroxy-ethyl)-methyl-(5-nitro-pyridin-2-yl)-amine (350 mg, 1.77 mmol) in THF (15 mL) and DMF (2 mL) was stirred with 60% NaH in oil (142 mg, 4.44 mmol) for 1 hr. The mixture was cooled and to this was added tert-butyl bromoacetate (1.31 mL, 8.88 mmol). The reaction mixture was allowed to stir overnight. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness and yielded 262 mg following flash chromatography. ES-MS calcd for C14H21N3O5 (m/e) 311.34, obsd 312 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with H2O
  3. dry with materialdried over MgSO4
  4. filtrationThe EtOAc layer was filtered
  5. customevaporated to dryness
  6. customyielded 262 mg

Sources & evidence

ORD record
ord-91beedfd02724d24978d7a70c237d0c5
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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