Pyridine → HCID 117653133, compound

HRID 2178115Notes

Reaction equation

HRID 2178115 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:20](Cl)(=[O:22])=[O:21])[CH:6]=[C:7]([F:19])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[C:12](F)[CH:11]=1)#[N:2].[F:24][C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=1.N1C=CC=CC=1.C(Cl)[Cl:39]>O>[Cl:39][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]#[N:17])[O:9][C:8]1[C:7]([F:19])=[CH:6][C:5]([S:20]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([F:24])=[CH:30][N:29]=2)(=[O:22])=[O:21])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 27377012-Amino-5-fluoropyridineHCID 117653399HCID 117653399, compound

Product 1

HCID 117653133HCID 117653133, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-cyano-4-(4-cyano-3-fluorophenoxy)-5-fluorobenzene-1-sulfonyl chloride (Preparation 43, 27 mg, 0.153 mmol) in DCM (5 mL) was added 5-fluoro-2-aminopyridine (26 mg, 0.230 mmol) followed by pyridine (36 mg, 0.459 mmol, 0.037 mL) and the reaction was stirred at room temperature for 18 hours. The reaction was diluted with DCM (20 mL) and water (30 mL). The organic layer was separated and the aqueous re-extracted with DCM (2×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase chromatography eluting with (acetonitrile/0.1% formic acid) and (water/0.1% formic acid), gradient 5% to 60% to afford the title compound as colourless solid (21 mg, 31%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous re-extracted with DCM (2×30 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase chromatography
  7. washeluting with (acetonitrile/0.1% formic acid) and (water/0.1% formic acid), gradient 5% to 60%

Sources & evidence

ORD record
ord-0f2c3735d384418c882a3193ce732341
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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