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

HRID 39517Notes

Reaction equation

HRID 39517 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-966ad8c21d74409184b0f895d9831b1a
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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