Potassium Fluoride → HCID 118036851, compound

HRID 1777878Notes

Reaction equation

HRID 1777878 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:3]=1.[F-:28].[K+]>CS(C)=O.CCOC(C)=O>[C:8]([C:7]1[C:2]([F:28])=[CH:3][C:4]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:5][CH:6]=1)#[N:9]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 118036382HCID 118036382, compound2×

Product 1

HCID 118036851HCID 118036851, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

N-(4-chloro-5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 2J, 106 mg, 0.273 mmol) and KF (159 mg, 2.73 mmol) were dissolved in DMSO (3 ml). The mixture was stirred at 110° C. for 16 h. The mixture was cooled to room temperature, diluted in EtOAc and washed with sat. aq. NaHCO3 (2×) and brine. The org. layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 60:40) to give the title compound as a white solid. (UPLC-MS 3) tR 1.20 min; ESI-MS 372.1 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with sat. aq. NaHCO3 (2×) and brine
  3. dry with materiallayer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 60:40)

Sources & evidence

ORD record
ord-e4927c8eb8674a879c63dcc8248d824a
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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