Trifluoromethanesulfonic anhydride → HCID 86677625, compound

HRID 476113Notes

Reaction equation

HRID 476113 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][C:17]([N:20]1[C:24]2[NH:25][C:26](=O)[CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23]=2[C:22]([CH3:35])=[N:21]1)([CH3:19])[CH3:18]>N1C=CC=CC=1.CCOC(C)=O>[CH3:19][C:17]([N:20]1[C:24]2[N:25]=[C:26]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23]=2[C:22]([CH3:35])=[N:21]1)([CH3:16])[CH3:18]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 136334041HCID 136334041, compound

Product 1

HCID 86677625HCID 86677625, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.457 mL, 2.70 mmol) was added dropwise to a solution of ethyl 1-(1,1-dimethylethyl)-3-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (500 mg, 1.803 mmol) in pyridine (10 mL), and the reaction mixture was stirred at room temperature for 16 h. The contents were diluted with EtOAc and washed with saturated NaHCO3, and then brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (0% to 100% DCM:Hex) to afford the final product as a solid, 670 mg (91%). LCMS E-S (M+H)=410.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (t, J=7.07 Hz, 3H), 1.71 (s, 9H), 2.58 (s, 3H), 4.46 (q, J=7.07 Hz, 2H), 7.63 (s, 1H).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via silica gel chromatography (0% to 100% DCM:Hex)

Sources & evidence

ORD record
ord-ae5944fbf30649bc8c7f65be6c61f363
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…