Water → HCID 69520328, compound

HRID 1179931Notes

Reaction equation

HRID 1179931 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].N12CCN(CC1)CC2.O>O1CCCC1.CCCCCCC>[CH3:13][C:11]([CH3:12])([CH3:14])[CH2:10][C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:18](=[O:19])[N:17]([CH3:16])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:7][CH:6]=1)=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178445144HCID 178445144, compound

Product 1

HCID 69520328HCID 69520328, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-3,3-dimethyl-butyramide (0.42 g, 2.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.37 g, 2.20 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.25 g, 2.20 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature for 2.5 hours. Water was added and the solution was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was redissolved in ethyl acetate and the solution was filtered over a short pad of silicagel. Evaporation of the solvent and crystallisation of the solid from ethyl acetate:heptane yielded the title compound (0.54 g, 79% yield) as a white solid.

Workup

  1. extractionthe solution was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. filtrationthe solution was filtered over a short pad of silicagel
  7. customEvaporation of the solvent and crystallisation of the solid from ethyl acetate

Sources & evidence

ORD record
ord-17b24aa2297e4281a8f500637c933300
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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