Triethylamine → HCID 25126887, compound

HRID 1672756Notes

Reaction equation

HRID 1672756 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH:15]3[N:11]([CH2:12][CH2:13][CH2:14]3)[C:10]3[N:17]=[C:18]([NH:21][CH2:22][CH3:23])[N:19]=[CH:20][C:9]=3[C:8]2=[O:24])=[CH:4][CH:3]=1.Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:22]([NH:21][C:18]1[N:19]=[CH:20][C:9]2[C:8](=[O:24])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)=[CH:26][CH:25]=3)[CH2:16][C@H:15]3[N:11]([CH2:12][CH2:13][CH2:14]3)[C:10]=2[N:17]=1)[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 67350133HCID 67350133, compound

Product 1

HCID 25126887HCID 25126887, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 6 (80.0 mg, 0.227 mmol) obtained in Example 6 was dissolved in dichloromethane (5 mL), and the mixture was stirred at room temperature for 1.5 hours after adding nicotinoyl chloride.hydrochloride (61.0 mg, 0.340 mmol) and triethylamine (0.095 mL, 0.340 mmol). Thereafter, an aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give the title compound (Compound 7) (54.3 mg, 52%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue obtained upon concentration under reduced pressure
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f0cd0c618a5f49e08f9fbef2e3f201d9
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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