Triethylamine → HCID 58938679, compound

HRID 598172Notes

Reaction equation

HRID 598172 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[C:16](=[O:18])[C:15]([C:19](O)=[O:20])=[CH:14][N:13]([CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[C:12]=2[N:11]=[CH:10]1.C(N(CC)CC)C.ClC(OCC)=O.C(=O)([O-])[O-].[BH4-].[Na+]>C1COCC1.C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[C:16](=[O:18])[C:15]([CH2:19][OH:20])=[CH:14][N:13]([CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[C:12]=2[N:11]=[CH:10]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19660Carbonate IonHCID 4311764Sodium borohydrideHCID 58938691HCID 58938691, compound

Product 1

HCID 58938679HCID 58938679, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.14 g (0.29 mmol) of 1-(2,4-dimethylphenyl)-4-(heptan-4-yl)-7-oxo-4,7-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxylic acid in 5 mL of THF was added 0.15 mL (1.1 mmol) of triethylamine and 0.10 mL (1.0 mmol) of ethyl chloroformate. The resulting yellow slurry was stirred at room temperature for 40 min. The crude carbonate solution was then added to 0.135 g (3.6 mmol) of sodium borohydride in 5 mL of ethanol at room temperature and the resulting mixture was stirred for 30 min. The reaction was concentrated in vacuo, diluted with water and extracted with chloroform. The combined extracts were washed with brine, dried over sodium sulfate, filtered and the resulting filtrate was concentrated in vacuo. The crude material thus obtained was purified by flash chromatography eluting with a 3% methanol/dichloromethane mixture to give 45 mg of the title compound as a white solid. Dirty fractions were combined, concentrated and purified to give an additional 23 mg of the title compound. The overall yield of the title compound was 68 mg (65%).

Workup

  1. stirringthe resulting mixture was stirred for 30 min
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with chloroform
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe resulting filtrate was concentrated in vacuo
  9. customThe crude material thus obtained
  10. customwas purified by flash chromatography
  11. washeluting with a 3% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-e0e5d4ea58264578982ad5a7ba8f2351
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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