Dichloromethane → HCID 86589212, compound

HRID 1179934Notes

Reaction equation

HRID 1179934 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[N:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=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.[Cl:37]CCl>O1CCCC1.CCCCCCC>[Cl:37][C:4]1[N:5]=[CH:6][C: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])=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178522258HCID 178522258, compound

Product 1

HCID 86589212HCID 86589212, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-nicotinamide (0.56 g, 2.25 mmol), N-methyl-N-phenylcarbamoyl chloride (0.51 g, 3.00 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.67 g, 6.00 mmol) in dry tetrahydrofuran (15 mL) was stirred at room temperature for 1 hour. Dichloromethane was added and the solution was extracted twice with water. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 70:30) followed by crystallised from ethyl acetate:heptane, yielding the title compound (44 mg, 5% yield) HPLC-MS (Method A): m/z=383 (M+H)+; Rt=3.40 min.

Workup

  1. extractionthe solution was extracted twice with water
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 70:30)
  6. customby crystallised from ethyl acetate

Sources & evidence

ORD record
ord-1f5a72b575654e1ca1a557083252c993
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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