Trifluoroacetic acid → HCID 178515762, compound

HRID 1890318Notes

Reaction equation

HRID 1890318 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]([F:19])([F:18])[F:17].[CH:21](OC)(OC)OC.FC(F)(F)C(O)=O>CO>[F:18][C:16]([F:19])([F:17])[O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[C:7]2=[N:6][C:5]([OH:20])=[CH:4][CH:3]=[C:2]2[N:1]=[CH:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 178507772HCID 178507772, compound

Product 1

HCID 178515762HCID 178515762, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-amino-6-(2-(trifluoromethoxy)phenylamino)pyridin-2-ol (75.0 mg, 0.26 mmol) dissolved in MeOH was added trimethyl orthoformate (1.0 mL, 9.05 mmol) and catalytical amount of trifluoroacetic acid. The solution was stirred at room temperature overnight and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (78 mg). LCMS m/z=296.0 [M+H]+, 1H NMR (400 MHz, DMSO-d6) δ ppm 6.63 (d, J=8.6 Hz, 1H), 7.66 (m, 3H), 7.81 (d, J=7.6 Hz, 1H), 8.03 (d, J=8.6 Hz, 1H), 8.42 (s, 1H), 10.60-11.20 (broad s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1b7fbee0753e4669b59659490a0870b2
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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