Formaldehyde → HCID 21190137, compound

HRID 619473Notes

Reaction equation

HRID 619473 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[N:17]2[CH:18]=[CH:19][N:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1)=[O:4].[CH2:23]=O>C(O)(=O)C>[F:22][C:2]([F:21])([F:1])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][C:12]2[N:17]3[C:18](=[CH:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)[CH2:23]1)=[O:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21190157HCID 21190157, compound

Product 1

HCID 21190137HCID 21190137, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3860 mg (12.28 mmol) of 5-[N-(4-trifluoroacetamidobutan-1-yl)aminomethyl]imidazo[1,2-a] pyridine in 15 ml of acetic acid was added 13.8 ml (184.21 mmol) of a 37% aqueous solution of formalin. The mixture was heated for 30 minutes at 100° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in 100 ml of purified water. To this solution was added 2N sodium hydroxide to adjust the pH to 8, and extracted with 150 ml of dichloromethane. The organic layer was washed with 200 ml of a saturated aqueous saline solution, and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to afford 2890 mg of the desired compound (72.0%, a white solid).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 100 ml of purified water
  3. additionTo this solution was added 2N sodium hydroxide
  4. extractionextracted with 150 ml of dichloromethane
  5. washThe organic layer was washed with 200 ml of a saturated aqueous saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-6b87061eee774484b8546a215b4af215
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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