Picolinic acid → HCID 66691938, compound

HRID 710563Notes

Reaction equation

HRID 710563 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:31][C:32]1[CH:63]=[CH:62][C:61]([F:64])=[CH:60][C:33]=1[CH:34]=[C:35]1[CH2:40][CH2:39][N:38]([C:41]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([NH:50]C(NC3C=CC=CC=3)=O)=[CH:46][CH:45]=2)=[O:42])[CH2:37][CH2:36]1.CCN(CC)CC>ClCCl.O>[F:31][C:32]1[CH:63]=[CH:62][C:61]([F:64])=[CH:60][C:33]=1[CH:34]=[C:35]1[CH2:40][CH2:39][N:38]([C:41]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([NH:50][C:7](=[O:9])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:46][CH:45]=2)=[O:42])[CH2:37][CH2:36]1

Participants

8

Reactant 5

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66692527HCID 66692527, compound

Product 1

HCID 66691938HCID 66691938, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Picolinic acid (69.0 mg, 0.56 mmol) was dissolved in dichloromethane (4.0 mL), and then HOBt (70.0 mg, 0.56 mmol), WSC (107 mg, 0.56 mmol), the compound (200 mg, 0.37 mmol) obtained in Example 73 (1) and Et3N (103 μL, 0.74 mmol) were added thereto, followed by stirring at room temperature 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. After the desiccant was filtered off, 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 (132 mg, 79%) as a white solid.

Workup

  1. extractionafter extraction with chloroform
  2. washthe extract was washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-0785dfd26a3f44a59f44cd2467e269d7
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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