Sodium Bicarbonate → HCID 57592473, compound

HRID 1784417Notes

Reaction equation

HRID 1784417 reaction equation
C(O[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[S:14](Cl)(=[O:16])=[O:15])[CH2:10][N:9]([C:18](=O)[C:19](F)(F)F)[CH2:8][CH2:7]2)C.[F-:24].[K+].C(=O)(O)[O-].[Na+]>C(#N)C>[F:24][C:4]1[CH:5]=[CH:6][C:11]([S:14]([C:13]2[C:4]([N:9]([CH3:10])[CH3:8])=[CH:5][C:6]3[CH2:7][CH2:8][N:9]([CH3:10])[CH2:18][CH2:19][C:11]=3[CH:12]=2)(=[O:15])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 86601723HCID 86601723, compound

Product 1

HCID 57592473HCID 57592473, compoundYield 173.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-ethoxy-2-(2,2,2-trifluoro-ethanoyl)-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (0.34 g, 0.92 mmol) in acetonitrile (3.8 mL) was added potassium fluoride (0.28 g, 4.8 mmol) and 18-crown-16 (1 crystal). The mixture was stirred at room temperature overnight before addition of aqueous sodium bicarbonate to pH 8. The resulting mixture was extracted with ethyl acetate, dried over MgSO4 and evaporated to dryness yielding the subtitled compound as a white solid (0.29 g). MH−354. 1H NMR δ (CDCl3) 1.43-1.53 (3H, t), 2.95-3.07 (2H, m), 3.80-3.93 (2H, m), 4.14-4.26 (2H, m), 4.70-4.80 (2H, d), 6.82-6.90 (1H, d), 7.68-7.75 (1H, d).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-ad90a8a3971b45b2bc09b7a4f4292bd3
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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