Perchloric Acid → HCID 178515884, compound

HRID 729844Notes

Reaction equation

HRID 729844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([C:13]2[CH:14]=[N:15][C:16](F)=[CH:17][CH:18]=2)=[CH:10]OC)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl(O)(=O)(=O)=[O:21]>O1CCOCC1.O.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([OH:21])=[N:15][CH:14]=3)=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 24247Perchloric AcidHCID 670612005-Bromo-3-[1-(6-fluoro-pyridin-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine

Product 1

HCID 178515884HCID 178515884, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-3-[1-(6-fluoro-pyridin-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine (220 mg, 0.678 mmol) in 1,4-dioxane (3 ml) in a Smith process vial was added 0.3 ml of 70% aqueous perchloric acid. The reaction was irradiated in a Personal Chemistry® microwave to 150° C. for 300 s. The reaction mixture was diluted with water and neutralized to pH 7 by addition of an aqueous solution of sodium hydroxide. The resulting precipitate was filtered, washed with water, and dried in vacuo to yield the title compound as a beige solid (152 mg, 77% yield). 1H NMR (DMSO-d6): δ 12.1 (broad s, 1H), 11.7 (broad s, 1H), 8.32 (d, J=2.5 Hz, 1H), 8.30 (d, J=2.5 Hz, 1H), 7.83 (dd, J=2.5, 11.5 Hz, 1H), 7.82 (s, 2H), 7.67 (s, 1H), 6.43 (d, J=11.5 Hz, 1H); MS: m/z 290 [MH]+.

Workup

  1. customThe reaction was irradiated in a Personal Chemistry® microwave to 150° C. for 300 s
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dd3c543de31c4a08b810745e3a74688c
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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