Trifluoroacetic acid → HCID 178527557, compound

HRID 1500045Notes

Reaction equation

HRID 1500045 reaction equation
[F:1][C:2]1[C:3]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[N:4][C:5]([O:8]CC2C=CC=CC=2OC)=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[C:3]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59160627HCID 59160627, compound

Product 1

HCID 178527557HCID 178527557, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solid N-(5-fluoro-2-(2-methoxybenzyloxy)pyrimidin-4-yl)benzenesulfonamide (714 mg, 1.83 mmol) was dissolved in dichloromethane (10 mL) followed by the addition of trifluoroacetic acid (1.0 mL, 13.5 mmol) and allowed to stir at room temperature for 1 h. The solvent was removed in vacuo and the resulting residue was dissolved in dichloromethane:methanol in a 10:1 ratio. The product was purified by column chromatography (dichloromethane/methanol gradient) to yield N-(5-fluoro-2-hydroxypyrimidin-4-yl)benzenesulfonamide (251 mg, 51% yield) as a white solid: mp 221-223° C.; 1H NMR (300 MHz) δ 11.57 (bs, 1H), 11.11 (bs, 1H), 8.04 (d, J=6.1 Hz, 1H), 7.94-7.84 (m, 2H), 7.71-7.51 (m, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane
  3. customThe product was purified by column chromatography (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-d3e9e573e5814a0d8edf4bc4e9e851d0
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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