Formaldehyde → 4,5-Dihydro-4-(4-pentafluoropropionamidobutan-1-yl)-3H-1,4,8b-triazaacenaphthylene
Reaction equation
[F:1][C:2]([F:25])([C:21]([F:24])([F:23])[F:22])[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].[CH2:26]=O>C(O)(=O)C>[F:25][C:2]([F:1])([C:21]([F:23])([F:24])[F:22])[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)[CH2:26]1)=[O:4]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2620 mg (7.19 mmol) of 5-[N-(4-pentafluoropropionamidobutan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in 10 ml of acetic acid was added 8.1 ml (107.88 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 100 ml of dichloromethane. The organic layer was washed with 100 ml of a saturated aqueous saline solution, dried over magnesium sulfate, and distilled off the solvent under reduced pressure. The residue was purified by silica gel column chromatography to afford 2250 mg of the desired compound (83.2%, a pale yellow liquid).
Workup
- distillationThe solvent was distilled off under reduced pressure
- dissolutionthe residue was dissolved in 100 ml of purified water
- additionTo this solution was added 2N sodium hydroxide
- extractionextracted with 100 ml of dichloromethane
- washThe organic layer was washed with 100 ml of a saturated aqueous saline solution
- dry with materialdried over magnesium sulfate
- distillationdistilled off the solvent under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a2f03b49c8704cf89ef05b95ee851a27
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06251905B1
Reaction notes
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