Dimethylformamide → HCID 118598862, compound

HRID 1050415Notes

Reaction equation

HRID 1050415 reaction equation
Cl[C:2]1[CH:7]=[C:6](NC2N=CN=C(NC(C3CC3)=O)C=2)[C:5](=[O:21])[N:4]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29](F)C=3)(C)[NH:23][C:24](=[O:25])[C:3]=12.[H-].[Na+].[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][OH:45])=[CH:40][CH:39]=1.[CH3:46]N(C)C=O>>[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][O:45][C:6]2[C:5](=[O:21])[N:4]3[C:22]4([CH2:27][CH2:32][CH2:31][CH2:30][CH2:29]4)[NH:23][C:24](=[O:25])[C:3]3=[C:2]([CH3:46])[CH:7]=2)=[CH:40][CH:39]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 118598561HCID 118598561, compound

Product 1

HCID 118598862HCID 118598862, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 6′-bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (1, 2.5 g, 8.03 mmol) in dimethylformamide (20 mL), sodium hydride (1.15 g, 48.23 mmol) was added portion wise. The reaction mixture was stirred at 0° C. for 30 m. To the reaction mixture was added (4-methoxyphenyl)methanol (3.34 g, 24.11 mmol) and the reaction was stirred at 80° C. for 16 h. After completion, solvent was evaporated under reduced pressure. Obtained crude was washed with water (50 mL) followed by diethyl ether and dried under reduced pressure to afford 6′-((4-methoxybenzyl)oxy)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3) as yellow solid. Yield: 1.4 g, 48%; MS (ESI) m/z 369.15 [M+1]+.

Workup

  1. stirringthe reaction was stirred at 80° C. for 16 h
  2. customAfter completion, solvent was evaporated under reduced pressure
  3. customObtained crude
  4. washwas washed with water (50 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-e90e2b0b758a452fa388036da019092b
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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