HCID 66704216, compound → HCID 66704197, compound

HRID 424839Notes

Reaction equation

HRID 424839 reaction equation
[CH:1]([C:4]1[N:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=1[CH2:20][O:21][C:22]1[N:27]=[C:26]([CH3:28])[C:25]([N+:29]([O-])=O)=[CH:24][CH:23]=1)([CH3:3])[CH3:2]>CCO.C1COCC1.[Pt]=O>[CH:1]([C:4]1[N:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=1[CH2:20][O:21][C:22]1[N:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[CH:24][CH:23]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66704216HCID 66704216, compound

Product 1

HCID 66704197HCID 66704197, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a room temperature solution of 6-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-3-nitro-pyridine (2.78 g, 6.35 mmol) in EtOH/THF (1/1, 200 mL) is added platinum (II) oxide (144 mg, 0.636 mmol, 10 mol %). The mixture is stirred under an atmosphere of hydrogen gas. After 3 h, the reaction is filtered through diatomaceous earth. The filtrate is concentrated and the residue is chromatographed (SiO2 120 g, 0% to 30% EtOAc/Hexane to yield 6-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-pyridin-3-ylamine (2.28 g, 88%). 1H NMR (400 MHz, CDCl3) δ 7.57-7.51 (m, 2H), 7.46-7.38 (m, 2H), 6.92 (d, 1H, J=8.4 Hz), 6.26 (d, 1H, J=8.4 Hz), 5.25 (s, 2H), 3.29 (sept, 1H, J=7.0 Hz), 2.24 (s, 3H), 1.40 (d, 6H, J=7.0 Hz).

Workup

  1. filtrationthe reaction is filtered through diatomaceous earth
  2. concentrationThe filtrate is concentrated
  3. customthe residue is chromatographed (SiO2 120 g, 0% to 30% EtOAc/Hexane

Sources & evidence

ORD record
ord-9107b4855e864fedae83cc164577821b
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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