Trifluoroacetic acid → N-{[(2R)-2,3-dihydroxypropyl]oxy}-3-[(2-fluoro-4-iodophenyl)-amino]isonicotin-amide

HRID 218885Notes

Reaction equation

HRID 218885 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10](=[O:26])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])[CH2:4][O:3]1.FC(F)(F)C(O)=O>ClCCl>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57649624HCID 57649624, compound

Product 1

HCID 11640893N-{[(2R)-2,3-dihydroxypropyl]oxy}-3-[(2-fluoro-4-iodophenyl)-amino]isonicotin-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-[(2-fluoro-4-iodophenyl)amino]isonicotinamide (synthesis described below) (3.0 g, 6.16 mmol) in dichloromethane (20 mL) was treated with trifluoroacetic acid (20 mL) and the clear-yellow solution was stirred at room temp. After stirring for 8 h, the contents were concentrated to a yellow oil, which was dissolved in ethyl acetate (100 mL) and poured into water (150 mL). The pH of the biphasic mixture was adjusted between 6 and 7 with 2.0 N aqueous sodium hydroxide and the layers were separated. The organics were dried over sodium sulfate, concentrated to a yellow oil and placed under high vacuum at 40° C. The resultant yellow, solid foam weighed 2.39 g (5.34 mmol, 87%) after drying for 18 h. LC/MS [5.22 min; 448 (M+1)]

Workup

  1. stirringAfter stirring for 8 h
  2. concentrationthe contents were concentrated to a yellow oil, which
  3. dissolutionwas dissolved in ethyl acetate (100 mL)
  4. additionpoured into water (150 mL)
  5. customthe layers were separated
  6. dry with materialThe organics were dried over sodium sulfate
  7. concentrationconcentrated to a yellow oil
  8. customplaced under high vacuum at 40° C
  9. customafter drying for 18 h
  10. customLC/MS [5.22 min; 448 (M+1)]

Sources & evidence

ORD record
ord-f22409b046744b37886e9eba131988ca
Source dataset
uspto-grants-2012_06
Patent number
US08198457B2

Reaction notes

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