Triethylamine → HCID 68353156, compound

HRID 1475951Notes

Reaction equation

HRID 1475951 reaction equation
[CH2:1]([NH:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:2][CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:7]([N:6]([CH2:1][CH2:2][CH:3]([CH3:4])[CH3:5])[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10988DiisoamylamineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 68353156HCID 68353156, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of diisopentylamine (5.0 ML, 24.7 mmol) and triethylamine (9.4 mL, 67.4 mmol) in dichloromethane (23 mL) at 0° C. was added slowly isonicotinoyl chloride hydrochloride (4 g, 22.5 mmol). The mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours. The mixture was diluted with saturated sodium bicarbonate and the separated aqueous layer was extracted with methylene chloride (3×25 mL). The combined organics were washed with water (10 mL), brine, dried (anh. sodium sulfate), filtered and evaporated. The residue solidified upon standing to afford 4.7 g of an orange solid. LCMS m/z 263.2 (M+H)+.

Workup

  1. extractionthe separated aqueous layer was extracted with methylene chloride (3×25 mL)
  2. washThe combined organics were washed with water (10 mL), brine
  3. dry with materialdried (anh. sodium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c8029e57d6ac4cc489596b7845f8e198
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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