Triethylamine → HCID 11998451, compound

HRID 2261177Notes

Reaction equation

HRID 2261177 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:10].[CH3:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18](Cl)=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([N:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[O:1][C:2]2=[O:10])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-oneHCID 152215164-Methylpiperidine-1-carbonyl Chloride

Product 1

HCID 11998451HCID 11998451, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg (0.735 mmol) of 3H-oxazolo[4,5-b]pyridin-2-one, 235 mg (1.45 mmol) of 4-methylpiperidine-1-carbonyl chloride and 101 μl (2.18 mmol) of triethylamine were stirred in 5 ml of pyridine at room temperature for 3 h. The reaction mixture was concentrated, and the residue was dissolved in water and extracted with ethyl acetate. The organic phase was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 6 mg (3%), M+H+: 262.12.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-821277f495164de18ef6a73f4d7c35e7
Source dataset
uspto-grants-2010_12
Patent number
US07846943B2

Reaction notes

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