Trifluoroacetic acid → HCID 178432222, compound

HRID 1890338Notes

Reaction equation

HRID 1890338 reaction equation
C([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)C1C=CC=CC=1.[C:23](O)([C:25](F)(F)F)=O>C(OC)(OC)(OC)C>[CH3:23][C:25]1[N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13]2=[N:14][C:9]([OH:8])=[CH:10][CH:11]=[C:12]2[N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67312740HCID 67312740, compound

Product 1

HCID 178432222HCID 178432222, compound

Reagents, catalysts & solvents 1

HCID 15050Trimethyl orthoacetateSolvent

Procedure

6-(Benzyloxy)-N2-phenylpyridine-2,3-diamine (68 mg, 0.23 mmol) was dissolved in trimethyl orthoacetate (5.0 mL) and TFA (10 μL) was added. The mixture was stirred at room temperature for 2 h and concentrated in vacuo. The benzyl group of the residue was then removed as described in Example 1.11, Step B to give the title compound as a white solid (15 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.35 (s, 1H), 6.51 (d, J=8.6 Hz, 1H), 7.48-7.55 (m, 3H), 7.57-7.63 (m, 2H), 7.84 (d, J=8.6 Hz, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe benzyl group of the residue was then removed

Sources & evidence

ORD record
ord-372f9ee127a44bdf98c67b3fd111dc73
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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