Npc316347 → HCID 58266529, compound

HRID 1888566Notes

Reaction equation

HRID 1888566 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Br:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[CH:20][C:19]=2[NH2:26])[C:14](F)=[N:15][CH:16]=1>C1COCC1.O>[CH3:25][O:24][C:22]1[N:21]=[CH:20][C:19]2[NH:26][C:14]3[N:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]=3[C:18]=2[CH:23]=1

Participants

5

Reactant 2

HCID 3280088Npc316347HCID 582665195-Bromo-2-fluoro-6'-methoxy-[3,4]bipyridinyl-3'-ylamine

Product 1

HCID 58266529HCID 58266529, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 1N solution of bis(trimethylsilyl)amide in THF (6.81 mL, 6.81 mmol) was added dropwise to a solution of 5-bromo-2-fluoro-6′-methoxy-[3,4′]bipyridinyl-3′-ylamine (203 mg, 0.681 mmol) in THF (12.0 mL). The reaction mixture was stirred for 30 minutes at ambient temperature, diluted with water, and extracted into ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and methanol, absorbed onto silica gel, and purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in hexanes) to provide the title compound as an orange-tan solid (89.0 mg, 47%). 1H NMR (DMSO-D6, 400 MHz): 12.44-12.12 (m, 1H), 7.79 (d, J=2.6 Hz, 1H), 7.66 (d, J=3.5 Hz, 2H), 6.56 (s, 1H), 3.75 (s, 3H). LCMS (Method B): RT=1.83 min, M+H+=278/280.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in ethyl acetate
  6. custommethanol, absorbed onto silica gel
  7. custompurified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-087a7ae950564beb86f348830454c808
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

Loading…