Dichloromethane → HCID 58001797, compound

HRID 1943191Notes

Reaction equation

HRID 1943191 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([O:16][CH3:17])[N:10]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(Cl)Cl>CN(C=O)C>[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([NH:15][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13][CH:12]=[C:11]([O:16][CH3:17])[N:10]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 58001800N2-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyridine-2,3-diamine

Product 1

HCID 58001797HCID 58001797, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude N2-(2,2-dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)-2,3-pyridinediamine prepared in Example 16A(c) (assumed 123.6 mmol) was dissolved in anhydrous DMF (500 ml) under argon and anhydrous potassium carbonate (37.56 g, 2.2 eq.) was added, followed by ethyl bromoacetate (12.31 ml, 0.9 eq.). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the resulting reddish-brown slurry was partitioned between DCM (1.2 L) and water (300 ml). The organic phase was separated and washed with water (300 ml), dried over sodium sulphate, filtered and evaporated under reduced pressure to give a dark red oil, this was taken up in a minimum of DCM and purified by column chromatography on silica (eluted with 5%-60% ethyl acetate in petroleum ether)) (40-60°)). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a dark orange oil (35.42 g, 84%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting reddish-brown slurry was partitioned between DCM (1.2 L) and water (300 ml)
  3. customThe organic phase was separated
  4. washwashed with water (300 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a dark red oil
  9. custompurified by column chromatography on silica (eluted with 5%-60% ethyl acetate in petroleum ether)) (40-60°))
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ccbea56a33bc4f7689808a497e3a2103
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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