Hydrochloric Acid → HCID 59255450, compound

HRID 78231Notes

Reaction equation

HRID 78231 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][C:7]=1[F:20].O1CCCC1.Cl.C(=O)([O-])O.[Na+]>CO>[F:20][C:7]1[CH:8]=[C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:18]=[CH:19][C:6]=1[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 592555252-(4-[1,3]Dioxolan-2-yl-3-fluorobenzyloxy)-pyridine

Product 1

HCID 59255450HCID 59255450, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-[1,3]dioxolan-2-yl-3-fluoro-benzyloxy)-pyridine (2.17 g, 7.88 mmol) described in Manufacturing Example 204-1-4 in methanol (10 mL) and tetrahydrofuran (10 mL) was added 5 N hydrochloric acid (8.43 mL, 8.43 mmol). This solution was stirred for 15 minutes at room temperature. This mixture was cooled to 0° C. and neutralized with a saturated sodium hydrogencarbonate aqueous solution, after which it was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.81 g). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureThis mixture was cooled to 0° C.
  2. extractionafter which it was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-2895c6f8c938450e96db71ca1a1060cb
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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