Sodium Bicarbonate → HCID 58190579, compound

HRID 1892416Notes

Reaction equation

HRID 1892416 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][O:6]/[N:7]=[C:8](/[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([CH2:19][C:20]3[C:21]([F:31])=[C:22]4[C:27](=[CH:28][C:29]=3[F:30])[N:26]=[CH:25][CH:24]=[CH:23]4)=[N:17][N:18]=2)[N:15]=1)\[CH3:9].COCCN(S(F)(F)[F:42])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:42][CH2:2][CH2:3][CH2:4][CH2:5][O:6]/[N:7]=[C:8](/[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([CH2:19][C:20]3[C:21]([F:31])=[C:22]4[C:27](=[CH:28][C:29]=3[F:30])[N:26]=[CH:25][CH:24]=[CH:23]4)=[N:17][N:18]=2)[N:15]=1)\[CH3:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58190571HCID 58190571, compound

Product 1

HCID 58190579HCID 58190579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-1-(3-((5,7-difluoroquinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone O-4-hydroxybutyl oxime (30 mg, 0.070 mmol) (example 65) in 4 mL of DCM at −78° C. was added bis(2-methoxyethyl)aminosulfur trifluoride (180 mg, 0.813 mmol). The mixture was stirred at this temperature for 1 h, and stirred at it overnight. The mixture was poured into saturated aqueous NaHCO3, extracted with DCM, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with DCM/methanol afforded the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.94 (s, 1H), 8.37 (d, 1H), 7.98 (d, 1H), 7.81 (d, 1H), 7.63 (d, 1H), 7.44 (dd, 1H), 4.81 (s, 2H), 4.58-4.57 (m, 1H), 4.45 (t, 1H), 4.32 (t, 2H), 2.26 (s, 3H), 1.90-1.78 (m, 4H). LCMS (method A): [MH]+=429, tR=5.239 min.

Workup

  1. stirringstirred at it overnight
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbca03fd7e6143d3a2baa26b1e667206
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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