Dimethylamine → HCID 18983845, compound

HRID 1440476Notes

Reaction equation

HRID 1440476 reaction equation
[C:1](#N)C.C=O.[CH3:6][NH:7][CH3:8].[C:9]1([C:15]2[N:16]=[C:17]3[C:22]([C:23]([NH:25][CH:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[C:27]#[N:28])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]3[CH:36]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)(=O)C>[CH3:6][N:7]([CH2:1][C:36]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([C:23]([NH:25][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[C:27]#[N:28])=[O:24])[C:17]2=[N:16][C:15]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 6342AcetonitrileHCID 18983855HCID 18983855, compound

Product 1

HCID 18983845HCID 18983845, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To acetonitrile (10 ml) were added 37% formaldehyde (0.3 ml) and acetic acid (0.4 ml), and 50% aqueous solution of dimethylamine (0.3 ml) was added slowly thereto at 0° C. with stirring. To the mixture was added α-(2-phenyl-imidazo[1,2-a]pyridin-8-ylcarbonylamino)-(3-fluorophenyl)acetonitrile (1.0 g, 2.7 m moles), and the mixture was reacted at 50° C. for 2 hours and further stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was neutralized with saturated aqueous solution of NaHCO3. The solution was extracted with dichloromethane, and the extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel (eluent: chloroform) to give the object compound (0.47 g, yield 40.8%) as crystals. m.p. 123°-124° C.

Workup

  1. additionwas added slowly
  2. customthe mixture was reacted at 50° C. for 2 hours
  3. stirringfurther stirred at room temperature for 2.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionThe solution was extracted with dichloromethane
  6. washthe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by column chromatography on silica gel (eluent: chloroform)

Sources & evidence

ORD record
ord-7f6a3085cb6b40809d7c89359f578f40
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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