Ammonium Chloride → HCID 117653151, compound

HRID 2178120Notes

Reaction equation

HRID 2178120 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][C:7]1[N:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:29]([C:31]1[CH:32]=[C:33]([S:38](Cl)(=[O:40])=[O:39])[CH:34]=[CH:35][C:36]=1[F:37])#[N:30].[NH4+].[Cl-]>C1COCC1>[C:29]([C:31]1[CH:32]=[C:33]([S:38]([N:6]([CH2:5][C:4]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:3]=2[O:2][CH3:1])[C:7]2[N:8]=[N:9][CH:10]=[CH:11][CH:12]=2)(=[O:40])=[O:39])[CH:34]=[CH:35][C:36]=1[F:37])#[N:30]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 27789083-Cyano-4-fluorobenzenesulfonyl chlorideHCID 63362875HCID 63362875, compound

Product 1

HCID 117653151HCID 117653151, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a suspension of N-(2,4-dimethoxybenzyl)pyridazin-3-amine (Preparation 19, 1.0 g, 4.00 mmol) in THF (15 mL) at −20° C. was slowly added LiHMDS (1M, 4.0 mL, 4.00 mmol). The reaction mixture was left to stir at −20° C. for 30 minutes and then cooled to −78° C. To the reaction mixture was slowly added 3-cyano-4-fluorobenzene-1-sulfonyl chloride (0.8 g, 3.64 mmol) suspended in THF (15 mL). The reaction mixture was slowly warmed to room temperature and left at room temperature for 18 hours. To the vessel was added saturated aqueous NH4Cl solution (30 mL) and the product was extracted with EtOAc (25 mL). The organic layer was washed with saturated brine (40 mL), dried over MgSO4, and the solvent removed under vacuum. The residue was purified using silica gel column chromatography eluting with 70% EtOAc in heptanes to afford the title compound as an orange oil (561 mg, 36%).

Workup

  1. waitThe reaction mixture was left
  2. temperaturecooled to −78° C
  3. temperatureThe reaction mixture was slowly warmed to room temperature
  4. waitleft at room temperature for 18 hours
  5. extractionthe product was extracted with EtOAc (25 mL)
  6. washThe organic layer was washed with saturated brine (40 mL)
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum
  9. customThe residue was purified
  10. washeluting with 70% EtOAc in heptanes

Sources & evidence

ORD record
ord-ff9016a948c945e49b01aeddd44a0276
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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