Pyridinium hydrochloride → HCID 16049155, compound

HRID 506958Notes

Reaction equation

HRID 506958 reaction equation
[C:1]1([NH:11][C:12]2[CH:13]=[C:14]([C:20]3[N:25]=[C:24](CNC(=O)OC(C)(C)C)[CH:23]=[N:22][CH:21]=3)[CH:15]=[N:16][C:17]=2[O:18]C)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl.[NH+:36]1C=CC=C[CH:37]=1>C([O-])([O-])=O.[Na+].[Na+]>[C:1]1([NH:11][C:12]2[C:17](=[O:18])[NH:16][CH:15]=[C:14]([C:20]3[CH:21]=[N:22][CH:23]=[C:24]([NH:36][CH3:37])[N:25]=3)[CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 67423639HCID 67423639, compound

Product 1

HCID 16049155HCID 16049155, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

tert-butyl 6-(5-(isoquinolin-1-ylamino)-6-methoxypyridin-3-yl)pyrazin-2-ylmethylcarbamate (75 mg, 0.16 mmol, 1 eq.) and pyridinium hydrochloride (378 mg, 3.27 mmol, 20 eq.) were stirred at 150° C. for 10 minutes, allowed to cool to Rt and diluted with sat. Na2CO3 (10 mL). The resulting suspension was sonicated and filtered. The solid collected was washed with water (3×10mL), iso-propanol (1×5mL), diethyl ether (3×10 mL) and pentane (3×10 mL) to give a light brown powder (14.9 mg, 27% Yield).

Workup

  1. temperatureto cool to Rt
  2. customThe resulting suspension was sonicated
  3. filtrationfiltered
  4. customThe solid collected
  5. washwas washed with water (3×10mL), iso-propanol (1×5mL), diethyl ether (3×10 mL) and pentane (3×10 mL)

Sources & evidence

ORD record
ord-5995e534c4994ec1a655026b39467b69
Source dataset
uspto-grants-2010_08
Patent number
US07786130B2

Reaction notes

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