Trifluoroacetic acid → HCID 67312864, compound

HRID 1890337Notes

Reaction equation

HRID 1890337 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH2:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](O)(C(F)(F)F)=O>>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:23]=[N:22][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67312740HCID 67312740, compound

Product 1

HCID 67312864HCID 67312864, compound

Procedure

6-(Benzyloxy)-N2-phenylpyridine-2,3-diamine (60 mg, 0.21 mmol) was dissolved in trimethyl orthformate (5.0 mL), and TFA (10 μL) was added. The mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound as a red solid (58 mg). 1H NMR (500 MHz, CDCl3) δ ppm 5.40 (s, 2H), 7.15 (d, J=9.0 Hz, 1H), 7.31-7.42 (m, 5H), 7.62-7.72 (m, 5H), 8.32 (d, J=9.0 Hz, 1H), 9.25 (s, 1H).

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9775b7a87aaa4d23a7a819683a2957af
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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