Formaldehyde → HCID 21190149, compound

HRID 619425Notes

Reaction equation

HRID 619425 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[N:6]2[CH:26]=1)[CH3:2].[CH2:27]=O>C(O)(=O)C>[CH2:1]([C:3]1[N:4]=[C:5]2[N:6]3[C:7]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:21])[CH2:27][C:26]=13)=[CH:8][CH:9]=[CH:10]2)[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21190208HCID 21190208, compound

Product 1

HCID 21190149HCID 21190149, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 785 mg (2.00 mmol) of 2-ethyl-5-[N-[5-(trifluoromethanesulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 5 ml of acetic acid was added 2.25 ml (30.00 mmol) of a 37% aqueous solution of formalin. The mixture was heated for 30 minutes at 100° C. The solvent was then distilled off under reduced pressure. The residue was dissolved in 100 ml of a saturated aqueous solution of potassium carbonate. This solution was neutralized, under ice-cooling, with 1N HCl, which was 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 column chromatography (eluent: chloroform/methanol=20:1) to give 527 mg of the desired compound (65.2%, colorless liquid).

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 carbonate
  3. temperaturecooling, with 1N HCl, which
  4. extractionwas 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 column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-4f817a6aa88e4083899a6e06ad065f18
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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