Trifluoroacetic acid → (3-Aminopyridin-2-yl){1-[3-(trifluoromethyl)phenyl]cyclobutyl}methanol

HRID 1620997Notes

Reaction equation

HRID 1620997 reaction equation
[OH:1][CH:2]([C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[CH2:20][CH2:19][CH2:18]1)[C:3]1[C:8]([NH:9]C(=O)OC(C)(C)C)=[CH:7][CH:6]=[CH:5][N:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:9][C:8]1[C:3]([CH:2]([C:17]2([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)[CH2:20][CH2:19][CH2:18]2)[OH:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89524814Tert-butyl 2-(hydroxy(1-(3-(trifluoromethyl)phenyl)cyclobutyl)methyl)-pyridin-3-ylcarbamate

Product 1

HCID 71523069(3-Aminopyridin-2-yl){1-[3-(trifluoromethyl)phenyl]cyclobutyl}methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 120D (96 mg, 0.229 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The resulting solution was stirred at room temperature for about 2 hours, and concentrated in vacuum. The residue was treated with saturated NaHCO3 and extracted with ethyl acetate three times. Combined organic phases were washed with water and brine sequentially, dried over Na2SO4, filtered, and concentrated. The residue was purified by prep-HPLC (Column: BOSTON-C18 20×250 mm 10 μm, eluent: water (0.05% NH4HCO3): acetonitrile, 1:1 to 5:95) (60 mg, 30%) to provide the title compound. LC-LC-MS: m/z (M+H) 323. 1H NMR (400 MHz, CDCl3): δ 7.78-7.80 (m, 1H), 7.35-6.99 (m, 4H), 6.82-6.86 (m, 1H), 6.58-6.61 (m, 1H), 4.77 (s, 1H), 3.00 (b, 3H), 2.69-2.82 (m, 2H), 2.14-2.27 (m, 2H), 1.65-1.95 (m, 2H).

Workup

  1. concentrationconcentrated in vacuum
  2. additionThe residue was treated with saturated NaHCO3
  3. extractionextracted with ethyl acetate three times
  4. washCombined organic phases were washed with water and brine sequentially
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC (Column

Sources & evidence

ORD record
ord-9ed5111f81364b7c8849868f96a07904
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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