Picolinic acid → HCID 66939708, compound

HRID 1257401Notes

Reaction equation

HRID 1257401 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]2[S:15][C:16]([CH3:30])=[C:17]([CH2:19][N:20]3[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[N:21]3)[N:18]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](O)=[O:38].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[CH3:30][C:16]1[S:15][C:14]([C:6]2[CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=[C:4]([CH2:3][NH:2][C:37]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=3)=[O:38])[CH:5]=2)=[N:18][C:17]=1[CH2:19][N:20]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[N:21]1

Participants

8

Reactant 5

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66939445HCID 66939445, compound

Product 1

HCID 66939708HCID 66939708, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution (3 mL) of the compound (200 mg, 0.43 mmol) obtained in Example 95f in N,N-dimethylformamide were added 2-pyridinecarboxylic acid (64 mg, 0.52 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (99 mg, 0.52 mmol), 1-hydroxybenzotriazole (80 mg, 0.52 mmol) and triethylamine (0.12 mL, 0.86 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=30/70) to give the title compound (79 mg, 35%) as a pale-orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=30/70)

Sources & evidence

ORD record
ord-faa3dc5d500d4dc5a079254a58c38820
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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