Trifluoroacetic acid → HCID 86728406, compound

HRID 2171424Notes

Reaction equation

HRID 2171424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][C:30]1[CH:31]=[N:32][C:33]([F:36])=[CH:34][CH:35]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[N:16](C(OC(C)(C)C)=O)[C:15]([CH3:25])([CH3:24])[CH2:14][N:10]2[C:11](=[O:13])[N:12]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][C:30]1[CH:31]=[N:32][C:33]([F:36])=[CH:34][CH:35]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[NH:16][C:15]([CH3:25])([CH3:24])[CH2:14][N:10]2[C:11](=[O:13])[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86728407HCID 86728407, compound

Product 1

HCID 86728406HCID 86728406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 7-((3-fluoro-4-((6-fluoropyridin-3-yl)oxy)benzyl)oxy)-2,2-dimethyl-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1(5H)-carboxylate (130 mg, 0.260 mmol) in dichloromethane (DCM) (4 mL) was added TFA (1.00 mL, 13.0 mmol) at 25° C. The reaction mixture was stirred at 25° C. overnight, concentrated and diluted with ethyl acetate/saturated sodium bicarbonate solution. Organic layer was separated, washed with water then saturated brine, dried over sodium sulphate. Purification via preparative TLC (DCM/MeOH=10/1) afforded the desired product as a white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate/saturated sodium bicarbonate solution
  3. customOrganic layer was separated
  4. washwashed with water
  5. dry with materialsaturated brine, dried over sodium sulphate
  6. customPurification via preparative TLC (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-62532464c591481197f0bb2b403f3242
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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