Hydrochloric Acid → HCID 25111871, compound

HRID 2242004Notes

Reaction equation

HRID 2242004 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]([F:27])=[C:15]4[C:20]=3[N:19]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:17]=[C:16]4[O:25][CH3:26])[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCCC1>[F:27][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[C:20]2[C:15]=1[C:16]([O:25][CH3:26])=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[N:19]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25111756HCID 25111756, compound

Product 1

HCID 25111871HCID 25111871, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-5-fluoro-4-methoxy-2-(trifluoro-methyl)quinoline (Step 3, 0.6 g, 1.56 mmol, 1 eq.) in tetrahydrofuran (20 mL) was added 2N aqueous HCl (6 mL). The resulting mixture was stirred at 70° C. for 5 hours. The reaction was cooled to room temperature, poured into 1N aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give 0.41 g of the desired product as a light yellow solid; MP=171-173 C; MS (ES) m/z (relative intensity): 343 (M+H)+ (100).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-12cb1efbe3b14a5f8dc97acc96795801
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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