Hydrochloric Acid → 6-[(2,6-difluorophenyl)amino]-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2192963Notes

Reaction equation

HRID 2192963 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.Cl.[F:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:21]=1[NH2:22].[O:28]1CCOCC1>>[F:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:21]=1[NH:22][C:6]1[C:5]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:4]=2[C:3]2[C:2](=[O:28])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 796472,6-DifluoroanilineHCID 59375375HCID 59375375, compound

Product 1

HCID 250957586-[(2,6-difluorophenyl)amino]-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one

Conditions

Temperature
150 °C

Procedure

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (70 mg, 0.26 mmol) in dioxane (2 mL) were added HCl (0.131 mL, 4 N in dioxane) and 2,6 difluoroaniline (67.7 mg, 0.524 mmol) and heated to 150° C. for 3 hr. The reaction was cooled and purified by reverse phase HPLC. 1H NMR (600 MHz, CD3OD) δ 9.66 (dd, 1H), 8.56 (s, 1H) 7.50 (m, 1H), 7.48 (m, 2H), 7.13 (m, 2H), 6.45 (dd, 1H). LRMS (ESI) calc'd for (C18H11F3N3O) [M+H]+, 342.1; found 342.0.

Workup

  1. temperatureThe reaction was cooled
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-9e511550cb384a71acf7a735a5ab7c9c
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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