Trifluoromethanesulfonic acid → HCID 178490706, compound

HRID 76308Notes

Reaction equation

HRID 76308 reaction equation
C([O:8][C:9]1=[CH:10][N:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[S:12]/[C:13]/1=[N:14]\[C:15](=[O:25])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])C1C=CC=CC=1.OS(C(F)(F)F)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:26]([N:11]1[CH:10]=[C:9]([OH:8])/[C:13](=[N:14]/[C:15](=[O:25])[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])/[S:12]1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 178490707HCID 178490707, compound

Product 1

HCID 178490706HCID 178490706, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 155 (500 mg, 1.16 mmol) in anhydrous CH2Cl2 (20 mL) was treated at 0° C. with triflic acid (1741 mg, 11.6 mmol) for 1 h. A saturated solution of sodium bicarbonate was added and the organic layer was separated, dried with anhydrous MgSO4 and concentrated under reduced pressure to afford 400 mg of crude material, which was used directly without purification in the next reactions. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.55-1.71 (m, 9 H), 3.77-3.87 (m, 3 H), 7.18 (d, J=9.1 Hz, 1 H), 7.54 (dd, J=8.9, 2.2 Hz, 1 H), 7.81 (d, J=2.4 Hz, 1 H), 8.65 (s, 1 H); MS (DCI/NH3) m/z 341 (M+H)+.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried with anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cbc5f7416ea4693a33f77ff5f4c4f5b
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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