Hydrochloric Acid → HCID 67499245, compound

HRID 661353Notes

Reaction equation

HRID 661353 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2([F:18])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:8]2([F:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67499172HCID 67499172, compound

Product 1

HCID 67499245HCID 67499245, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 1B (3.0 g, 11.04 mmol) in dioxane (50 mL) was added 3M HCl (50 mL). The reaction mixture was stirred overnight at ambient temperature, quenched with 3M NaOH (50 mL) and extracted with ethyl acetate. The organic layer was separated and concentrated. The resulting residue was chromatographed on silica gel eluting with 0%-30% ethyl acetate-hexane to obtain 95% pure desired product (2.6 g, 103%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ PPM 2.29-2.37 (M, 2H), 2.54-2.75 (M, 6H), 7.48 (DDD, J=8.14, 4.75, 1.02 HZ, 1H), 8.01 (DD, J=8.14, 1.70 HZ, 1H), 8.54 (D, J=4.75 HZ, 1H). MS (DCI) M/Z 228.01 (M+H)+.

Workup

  1. customquenched with 3M NaOH (50 mL)
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe resulting residue was chromatographed on silica gel eluting with 0%-30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-1e3d7996fe014e7da85f36d46903fdfc
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

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