Triethylamine → HCID 89996006, compound

HRID 1480835Notes

Reaction equation

HRID 1480835 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[C:10]([OH:17])[N:11]=[CH:12]3)[CH:4]=[N:3]1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20].C(N(CC)CC)C>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[S:19]([O:17][C:10]1[N:11]=[CH:12][C:13]2[C:8]([CH:9]=1)=[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)[N:16]=[CH:15][CH:14]=2)(=[O:20])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178480127HCID 178480127, compound

Product 1

HCID 89996006HCID 89996006, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(1-methyl-1H-pyrazol-4-yl)-2,6-naphthyridin-3-ol (Preparation 89, 15 mg, 0.066 mmol) in DCM (0.5 mL) was added Tf2O (0.013 mL, 0.080 mmol) and triethylamine (9.3 uL, 0.066 mmol). The reaction mixture was stirred at room temperature under 1 hour. The reaction mixture was concentrated in vacuo. The residue was passed through a SCX-2 cartridge eluting with 100% MeOH—1M NH3 in MeOH to give the title compound (14 mg, 59%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluting with 100% MeOH—1M NH3 in MeOH

Sources & evidence

ORD record
ord-1f2812c9063c446cb3e92e33b2ad03f1
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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