Pyridine → HCID 59435993, compound

HRID 1802505Notes

Reaction equation

HRID 1802505 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:27](=[N:29][OH:30])[NH2:28])[CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]1[C:18]2[CH:19]=[CH:20][N:21]=[C:22]([O:23][CH2:24][CH3:25])[C:17]=2[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[N:10]=1.N1C=CC=CC=1.[C:37]([O:40][C:41]([CH3:46])([CH3:45])[C:42](Cl)=O)(=[O:39])[CH3:38]>O1CCOCC1>[C:37]([O:40][C:41]([C:46]1[O:30][N:29]=[C:27]([C:4]2[CH:5]=[C:6]([Cl:26])[C:7]([NH:8][C:9]3[C:18]4[CH:19]=[CH:20][N:21]=[C:22]([O:23][CH2:24][CH3:25])[C:17]=4[C:16]4[C:11](=[CH:12][CH:13]=[N:14][CH:15]=4)[N:10]=3)=[C:2]([Cl:1])[CH:3]=2)[N:28]=1)([CH3:45])[CH3:42])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 136337086HCID 136337086, compound

Product 1

HCID 59435993HCID 59435993, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3,5-dichloro-4-[(10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]-N′-hydroxybenzenecarboximidamide (50 mg, 0.11 mmol) in 1,4-dioxane (1 mL) was added pyridine (0.1 mL) and 2-chloro-1,1-dimethyl-2-oxoethyl acetate (0.016 mL, 0.11 mmol). The reaction was heated to 110° C. for 4 h in a sealed tube. After cooling to room temperature, the solvents were evaporated and the residue was dissolved in THF/MeOH, filtered and purified by reverse phase HPLC to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were evaporated
  3. dissolutionthe residue was dissolved in THF/MeOH
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-b5b59a804148446e973be928b4e72a42
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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