O-Phenylenediamine → HCID 178453618, compound

HRID 1524856Notes

Reaction equation

HRID 1524856 reaction equation
[C:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:25])OC(C)(C)C)[C:9]2[NH:10][CH:11]=[C:12]([C:14](F)(F)F)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32].[OH2:34].[C:35]1([CH3:45])[CH:40]=[CH:39][C:38](S(O)(=O)=O)=[CH:37][CH:36]=1>C1COCC1>[NH:32]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:33]=[C:14]1[C:12]1[N:13]=[C:9]([C@@H:8]([NH:18][C:19]([C@H:38]2[CH2:39][CH2:40][C@H:35]([CH2:45][NH:18][C:19](=[O:25])[O:34][C:1]([CH3:7])([CH3:6])[CH3:2])[CH2:36][CH2:37]2)=[O:25])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 178454145HCID 178454145, compound

Product 1

HCID 178453618HCID 178453618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude intermediate from Example 32 Part B was dissolved in THF (2 mL). 1,2-Phenylenediamine (41 mg, 0.38 mmol) and p-toluenesulfonic acid monohydrate (7.3 mg, 0.038 mmol) were added to the reaction. The reaction was stirred at rt for 6 h and the solvent removed in vacuo. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (silica gel, 0-100% EtOAc in hexane gradient) to yield 59 mg (37%), as a yellow solid. HRMS m/z Calc'd for C23H26N5O2 [M+H]+: 404.2087. Found 404.2079.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (silica gel, 0-100% EtOAc in hexane gradient)
  8. customto yield 59 mg (37%)

Sources & evidence

ORD record
ord-11a5c842a198458281106c307b2d8185
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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