Formaldehyde → HCID 21190105, compound

HRID 1068694Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2.52 g (6.91 mmol) of 5-[N-[5-(trifluoromethanesulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 8 ml of acetic acid was added 7.8 ml (103.7 mmol) of a 37% aqueous solution of formalin. The mixture was heated at 100° C. for 30 minutes. The solvent was then distilled off under reduced pressure. The residue was dissolved in 50 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 to give 1.79 g of the desired compound (69.0%, colorless liquid).

Workup

distillationThe solvent was then distilled off under reduced pressure
dissolutionThe residue was dissolved in 50 ml of a saturated aqueous solution of potassium carbonate
temperaturecooling, with 1N HCl, which
extractionwas extracted twice with 100 ml of chloroform
dry with materialThe organic layer was dried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silicagel column chromatography

Sources & evidence

ORD record: ord-cff06bfa947345be98b291dbf5d1098d
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251905B1

Reaction notes

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