Hydrochloric Acid → HCID 68732840, compound

HRID 1175112Notes

Reaction equation

HRID 1175112 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13].Cl.N1C(C)=CC(C)=CC=1C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CCOC(C)=O.CN(C=O)C>[CH3:16][C:11]([NH:10][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9])([CH3:17])[C:12]([O:14][CH3:15])=[O:13]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10472-Pyrazinecarboxylic acidHCID 79532,4,6-TrimethylpyridineHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68732840HCID 68732840, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-pyrazinecarboxylic acid (1.22 g, 9.8 mmol), methyl 2-amino-2-methylpropanoate.HCl (1.50 g, 9.8 mmol) and collidine (3.9 mL, 29.4 mmol) in CH2Cl2 (25 mL) was added HATU (4.47 g, 11.8 mmol) in one portion. After 2 h, DMF (5 mL) and CH2Cl2 (25 mL) was added in order to solubilize the reaction. After stirring an addition 3 h, the reaction was diluted with EtOAc and the washed with 1 N HCl, 1N NaOH, saturated NaHCO3, and brine. The organic layer was dried (Na2SO4), filtered and concentrated. The material was used without further purification. 1H NMR (300 MHz, CDCl3) δ 9.16 (d, J=1.4 Hz, 1H); 8.75 (d, J=2.4 Hz, 1H); 8.53 (dd, J=1.5, 2.5 Hz, 1H); 8.33 (s, 1H); 3.79 (s, 3H); 1.70 (s, 6H). LC/MS: Rt=1.45 min, ES+224 (Formic Acid method).

Workup

  1. customthe reaction
  2. additionan addition 3 h
  3. washthe washed with 1 N HCl, 1N NaOH, saturated NaHCO3, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was used without further purification

Sources & evidence

ORD record
ord-83df801e30f1482ca734d2ff7b3a6bc9
Source dataset
uspto-grants-2010_11
Patent number
US07838673B2

Reaction notes

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