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

HRID 78778Notes

Reaction equation

HRID 78778 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-d6e31891cae641508405b781d943959d
Source dataset
uspto-grants-2014_09
Patent number
US08841459B2

Reaction notes

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