3-Aminopyridine → HCID 15604847, compound

HRID 1710459Notes

Reaction equation

HRID 1710459 reaction equation
[CH3:1][C:2]1([CH3:19])[N:7]2[C:8]3[CH:9]=[C:10]([C:15](O)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C1COCC1.C(Cl)Cl.C1COCC1>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([NH:26][C:15]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:6]4[C:5](=[O:18])[NH:4][CH2:3][C:2]([CH3:19])([CH3:1])[N:7]4[C:8]=3[CH:9]=2)=[O:16])[CH:28]=1

Participants

8

Reactant 4

HCID 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 58767565HCID 58767565, compound

Product 1

HCID 15604847HCID 15604847, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a suspension of 24 mg (0.093 mmol) of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid in 2:1 CH2Cl2/THF (3 mL) was added 16 μL (0.19 mmol) oxalyl chloride followed by two drops of 10% DMF in THF. After stirring for 1 h, the mixture was concentrated and 1 mL of CH2Cl2 was added followed by 17 mg (0.19 mmol) of 3-aminopyridine and 33 μL (0.19) of diisopropylethylamine. The mixture was stirred overnight, concentrated, and chromatographed (0-8% MeOH in CH2Cl2) to provide 30 mg of the title compound. ESI-MS m/z 3335 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated
  2. addition1 mL of CH2Cl2 was added
  3. stirringThe mixture was stirred overnight
  4. concentrationconcentrated
  5. customchromatographed (0-8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7f116ee978e74ae4b31bd489be4bca98
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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