Water → HCID 69518254, compound

HRID 1831251Notes

Reaction equation

HRID 1831251 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:12]=[N:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21].N12CCN(CC1)CC2.O>CN(C)C=O>[CH:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:20](=[O:21])[N:19]([CH3:18])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13][CH:12]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178520227HCID 178520227, compound

Product 1

HCID 69518254HCID 69518254, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-cyclohexyl-N-(6-hydroxy-pyridin-3-yl)-acetamide (0.70 g, 3.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.51 g, 3.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.34 g, 3.00 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 1 hour. Water was added and the precipitates were collected by suction. The solids were dissolved in dichloromethane and the solution was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was crystallised from ethyl acetate:heptane yielding the title compound (0.79 g, 72% yield) as a brown solid.

Workup

  1. customthe precipitates were collected by suction
  2. dissolutionThe solids were dissolved in dichloromethane
  3. dry with materialthe solution was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-9e315e41b66b4d4b80bf2612f8561224
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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