Dimethylformamide → HCID 9814006, compound

HRID 747482Notes

Reaction equation

HRID 747482 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8]1[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=1.C[N:18](C)C=O.COC(OC)N(C)C.C1C[CH2:39][N:38]2[C:33](=[N:34]CCC2)CC1>CC(O)C>[NH2:18][C:33]1[N:34]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:7]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[CH:39][N:38]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59749682HCID 59749682, compound

Product 1

HCID 9814006HCID 9814006, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To 5-(2-furan-2-yl-2-oxo-ethyl)-1-methyl-1H-pyridin-2-one (8) (10.0 g, 46.04 mmol) obtained in Preparation Example 5 were added dimethylformamide (20 mL), N,N-dimethylformamide dimethyl acetal (9.21 mL, 69.06 mmol) and DBU (10.3 mL, 69.06 mmol), and the reaction mixture was stirred at 80° C. for about 5 hours and then allowed to cool. Next, to the reaction mixture was added 2-propanol (100 mL), and the reaction mixture was stirred at 8° C. for about 16 hours. The precipitated crystals were collected by filtration, washed with 2-propanol (45 mL), and then air-dried at 50° C. for 20 minutes to give 10.2 g of a crude product of the title compound (10) as pale yellow crystals (content 10.2 g, yield 82.3%).

Workup

  1. temperatureto cool
  2. stirringthe reaction mixture was stirred at 8° C. for about 16 hours
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with 2-propanol (45 mL)
  5. customair-dried at 50° C. for 20 minutes

Sources & evidence

ORD record
ord-e1bafa9e481c42d89490494d2d137642
Source dataset
uspto-grants-2008_07
Patent number
US07396928B2

Reaction notes

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