Formaldehyde → HCID 21190082, compound

HRID 619422Notes

Reaction equation

HRID 619422 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[N:5]2[CH:24]=1.[CH2:25]=O>C(O)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]2[N:5]3[C:6]([CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:21])([F:22])[F:23])(=[O:19])=[O:18])[CH2:25][C:24]=13)=[CH:7][CH:8]=[CH:9]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21190100HCID 21190100, compound

Product 1

HCID 21190082HCID 21190082, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

In 6 ml of acetic acid was dissolved 2.02 g (5.54 mmol) of 2-methyl-5-[N-[4-(trifluoromethanesulfonamido) butan-1-yl]aminomethyl]imidazo[1,2-a]pyridine. To the solution was added 6.2 ml (83.15 mmol) of a 37% aqueous solution of formalin, and the mixture was heated for 30 minutes at 100° C. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in 100 ml of a saturated aqueous solution of potassium carbonate. This solution was neutralized by the addition of 1N HCl under ice-cooling, which was extracted twice with 100 ml of chloroform. The extract was dried over magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by silica-gel column chromatography (eluent: chloroform/methanol=20:1) to afford 1.45 g of the desired compound (72.0%, colorless liquid).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of a saturated aqueous solution of potassium carbonate
  4. additionThis solution was neutralized by the addition of 1N HCl under ice-
  5. temperaturecooling
  6. extractionwhich was extracted twice with 100 ml of chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica-gel column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-c2fb3979d67b42fa99b5fd60bd9aa8d3
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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