Trifluoroacetic acid → 4-(5-(2-Amino-pyridin-3-yl)isoxazol-3-ylmethyl)phenol

HRID 1891535Notes

Reaction equation

HRID 1891535 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[NH2:25][C:20]1[C:19]([C:17]2[O:16][N:15]=[C:14]([CH2:13][C:12]3[CH:26]=[CH:27][C:9]([OH:8])=[CH:10][CH:11]=3)[CH:18]=2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 160615083-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

Product 1

HCID 251143864-(5-(2-Amino-pyridin-3-yl)isoxazol-3-ylmethyl)phenolYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (32 mg, 0.090 mmol) described in Example 1 and trifluoroacetic acid (1 mL) was added thioanisole (45 mg, 0.36 mmol) at room temperature, which was stirred for 2 hours at the same temperature. To a mixture of saturated aqueous sodium hydrogencarbonate solution and ethyl acetate was added the reaction mixture. The organic layer was separated and washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (24 mg, 100%).

Workup

  1. additionwas added the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=4:1)

Sources & evidence

ORD record
ord-7647125cfee4493d8a85c18f91772554
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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