2-Aminothiazole → HCID 15604848, compound

HRID 1710460Notes

Reaction equation

HRID 1710460 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[S:28][CH:29]=[CH:30][N:31]=1.N1C(C)=CC=CC=1C>CN(C=O)C.C1COCC1.C(Cl)Cl.C1COCC1>[S:28]1[CH:29]=[CH:30][N:31]=[C:27]1[NH:26][C:15]([C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:6]3[C:5](=[O:18])[NH:4][CH2:3][C:2]([CH3:1])([CH3:19])[N:7]3[C:8]=2[CH:9]=1)=[O:16]

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 79372,6-LutidineHCID 65578Oxalyl chlorideHCID 58767565HCID 58767565, compound

Product 1

HCID 15604848HCID 15604848, compoundYield 53.7%

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 19 mg (0.19 mmol) of 2-aminothiazole and 22 μL (0.19 mmol) of 2,6-lutidine. The mixture was stirred overnight, concentrated, and chromatographed (0-8% MeOH in CH2Cl2) to provide 17 mg of the title compound. ESI-MS m/z 340.9 [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-106eb74c87f544f1b73f7b96a1ca7861
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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