Npc316347 → HCID 58266529, compound

HRID 1506028Notes

Reaction equation

HRID 1506028 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-166abb756ab246abbc547ab26915e1c8
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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