p-Toluenesulfonic acid → HCID 89690902, compound

HRID 595444Notes

Reaction equation

HRID 595444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[C:17]([NH:19][CH:20]([CH3:22])[CH3:21])[C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[CH3:23][C:24]1C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)(OC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:18]=[C:17]([NH:19][CH:20]([CH3:22])[CH3:21])[C:12]([C:13]3[O:14][C:23]([CH3:24])=[N:16][N:15]=3)=[CH:11][N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89689549HCID 89689549, compound

Product 1

HCID 89690902HCID 89690902, compound

Reagents, catalysts & solvents 1

HCID 15050Trimethyl orthoacetateSolvent

Procedure

A solution of 6-((4-fluorophenyl)amino)-4-(isopropylamino)nicotinohydrazide (91) (100 mg) and PTSA (10 mg) in trimethyl orthoacetate (5 mL) was heated at 100° C., overnight. The reaction mixture was concentrated, diluted with EtOAc. The organic layer was washed with sat. NaHCO3 solution, water and brine solution. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by prep. HPLC to afford N2-(4-fluorophenyl)-N4-isopropyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine-2,4-diamine (Example 149)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with sat. NaHCO3 solution, water and brine solution
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material obtained
  9. customwas purified by prep

Sources & evidence

ORD record
ord-bf84a54fe4524464a3892cd7c204fd58
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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