Sodium Thiosulfate Pentahydrate → HCID 59375547, compound

HRID 2192979Notes

Reaction equation

HRID 2192979 reaction equation
[CH3:1][CH:2]([NH:7][C:8]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:16]=2[C:15]2[C:14](=[O:22])[NH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)[C:3]([CH3:6])([CH3:5])[CH3:4].C1C(=O)N([I:30])C(=O)C1.C(=O)([O-])O.[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[I:30][C:11]1[C:10]2[N:9]=[C:8]([NH:7][CH:2]([CH3:1])[C:3]([CH3:5])([CH3:6])[CH3:4])[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:16]=3[C:15]=2[C:14](=[O:22])[NH:13][CH:12]=1

Participants

6

Reactant 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 25098356HCID 25098356, compound

Product 1

HCID 59375547HCID 59375547, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-[(1,2,2-trimethylpropyl)amino]pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one (221 mg, 0.746 mmol) in acetic acid (7.5 mL), NIS (336 mg, 1.491 mmol) was added. After stirring for 2 h at room temperature, aqueous sodium hydrogen carbonate was added, and then aqueous sodium thiosulfate pentahydrate (5%) was added. The aqueous mixture was extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford 4-iodo-6-[(1,2,2-trimethylpropyl)amino]pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one as an orange solid. 1H NMR (500 MHz, C2D6SO) δ 11.58 (d, 1H), 11.00 (s, 1H), 8.74 (s, 1H), 8.47 (d, 1H), 7.94 (d, 1H), 7.84 (d, 1H), 4.93 (m, 1H), 1.23 (d, 3H), 0.99 (s, 9H). LRMS (ESI) calc'd for (C17H19IN4O) [M+H]+, 423.1; found 423.0.

Workup

  1. extractionThe aqueous mixture was extracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  5. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-b0e2debfde9a4fbdbb24bd0e803ac41e
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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