Triethylamine → HCID 66692757, compound

HRID 710562Notes

Reaction equation

HRID 710562 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1N=CN([C:13](N2C=NC=C2)=[O:14])C=1.CCN(CC)CC.ClC1C=C(C=CC=1OC)C[N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:39]([N:41]2[CH2:46][CH2:45][C:44](=[CH:47][C:48]3[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:49]=3[F:55])[CH2:43][CH2:42]2)=[O:40])[CH2:34][CH2:33]1>C(#N)C.O>[F:55][C:49]1[CH:50]=[CH:51][C:52]([F:54])=[CH:53][C:48]=1[CH:47]=[C:44]1[CH2:43][CH2:42][N:41]([C:39]([NH:38][CH:35]2[CH2:36][CH2:37][N:32]([C:13](=[O:14])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:33][CH2:34]2)=[O:40])[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 104392-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 66691939HCID 66691939, compound

Product 1

HCID 66692757HCID 66692757, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Aminopyridine (70.0 mg, 0.75 mmol) was dissolved in acetonitrile (4 mL), and then CDI (121 mg, 0.75 mmol) and Et3N (104 μL, 0.75 mmol) were added dropwise thereto at 0° C. After stirring at room temperature for 1 hour, the compound (250 mg, 0.67 mmol) obtained in Example 36 (1) and Et3N (312 μl, 2.25 mmol) were added to the mixture, followed by stirring at 60° C. overnight. Water was added to the reaction mixture, and after extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:50), thereby giving the title compound (80.0 mg, 24%) as a white solid.

Workup

  1. customat 0° C
  2. stirringby stirring at 60° C. overnight
  3. extractionafter extraction with chloroform
  4. washthe extract was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. customthe residue obtained by evaporation under reduced pressure
  8. customwas purified

Sources & evidence

ORD record
ord-42d8b026c70642ef9a7d4793c0a53b67
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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