Sodium Thiosulfate → HCID 67415216, compound

HRID 2192990Notes

Reaction equation

HRID 2192990 reaction equation
[CH3:1][CH:2]([CH3:24])[C@@H:3]([NH:8][C:9]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:17]=2[C:16]2[C:15](=[O:23])[NH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)[C:4]([F:7])([F:6])[F:5].C1C=C(Cl)C=C(C(OO)=[O:33])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][CH:2]([CH3:24])[C@@H:3]([NH:8][C:9]1[C:18]2[CH:19]=[CH:20][N+:21]([O-:33])=[CH:22][C:17]=2[C:16]2[C:15](=[O:23])[NH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)[C:4]([F:6])([F:5])[F:7]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 25096016HCID 25096016, compound

Product 1

HCID 67415216HCID 67415216, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one (20 mg, 0.059 mmol) in CH2Cl2 (8 mL) at 0° C. was added m-CPBA (60 mg, 0.268 mmol, 77% max) and allowed to stir for 2 hr. 10% sodium thiosulfate and sat. sodium bicarbonate were added to the reaction solution and stirred for 30 min. The layers were separated, the organic layer was dried with MgSO4, filtered, and concentrated. The residue was purified on reverse phase HPLC 100% H2O to 100% MeCN to afford 6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one 9-oxide. 1H NMR (600 MHz, CD3OD) δ 10.80 (s, 1H), 8.50 (d, 1H), 8.35 (d, 1H), 7.48 (d, 1H), 6.60 (d, 1H), 5.39 (m, 1H), 2.33 (m, 1H), 1.14 (d, 3H), 1.06 (d, 3H). LRMS (ESI) calc'd for (C16H16F3N4O2) [M+H]+, 353.1; found 353.1.

Workup

  1. stirringstirred for 30 min
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on reverse phase HPLC 100% H2O to 100% MeCN

Sources & evidence

ORD record
ord-faea4d1eb51e455a813cadfa5f9872a6
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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