4-Aminopyridine → HCID 22734266, compound

HRID 2084775Notes

Reaction equation

HRID 2084775 reaction equation
[C:1](/[CH:4]=[CH:5]/[C:6]1[C:11]2[CH2:12][C:13]3([O:18][C:10]=2[C:9]([O:19][CH3:20])=[CH:8][CH:7]=1)[CH2:17][CH2:16][CH2:15][CH2:14]3)([OH:3])=O.C(Cl)Cl.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:39][C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1>O.O1CCOCC1>[CH3:20][O:19][C:9]1[C:10]2[O:18][C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:12][C:11]=2[C:6](/[CH:5]=[CH:4]/[C:1]([NH:39][C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)=[O:3])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 22734155HCID 22734155, compound

Product 1

HCID 22734266HCID 22734266, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 90b (0.3 g) obtained in Step B was suspended in a mixed solvent of methylene chloride (6 ml) and dioxane (1 ml), and dicyclohexylcarbodiimide (DCC) (0.23 g) and 4-aminopyridine (0.11 g) were added thereto after cooling the suspension to 0° C., followed by stirring at room temperature for 6 hours. Water was added to the mixture followed by extraction with chloroform. The collected organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (chloroform) to give Compound 90 (0.22 g, 64.5%) as pale-yellow crystals.

Workup

  1. additionwere added
  2. extractionfollowed by extraction with chloroform
  3. washThe collected organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-488135ea6388416998890967f10041c4
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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