Formaldehyde → HCID 21190191, compound

HRID 619418Notes

Reaction equation

HRID 619418 reaction equation
[F:1][C:2]([F:23])([F:22])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[N:18]2[CH:19]=[CH:20][N:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1)(=[O:5])=[O:4].[CH2:24]=O>C(O)(=O)C>[F:23][C:2]([F:1])([F:22])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][C:13]2[N:18]3[C:19](=[CH:20][N:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)[CH2:24]1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21190201HCID 21190201, compound

Product 1

HCID 21190191HCID 21190191, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6.91 g (19.72 mmol) of 5-[N-[4-(trifluoromethanesulfonamido)butan-1-yl]aminomethyl]-imidazo[1,2-a]pyridine in 20 ml of acetic acid was added 22.1 ml (295.8 mmol) of a 37% aqueous solution of formaldehyde. The mixture was heated at 100° C. for 30 minutes. The solvent was then distilled off under reduced pressure, and the residue was dissolved in 100 ml of a saturated aqueous solution of potassium hydrogencarbonate. This solution was neutralized, under ice-cooling, with 1N HCl, which was subjected to extracted twice with 100 ml of chloroform. The organic layer was dried over magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by silicagel chromatography (eluent: chloroform/methanol=20:1) to give 4.86 g (68.0%, pale yellow liquid product).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 100 ml of a saturated aqueous solution of potassium hydrogencarbonate
  3. temperaturecooling, with 1N HCl, which
  4. extractionto extracted twice with 100 ml of chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silicagel chromatography (eluent: chloroform/methanol=20:1)
  8. customto give 4.86 g (68.0%, pale yellow liquid product)

Sources & evidence

ORD record
ord-c009aa7ad0884b6c94bfb64b5986efb8
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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