proline dl-form → HCID 59375399, compound

HRID 2192980Notes

Reaction equation

HRID 2192980 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]([NH:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:8]3[C:9](I)=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[CH3:25][S:26]([O-:28])=[O:27].[Na+].N1CCCC1C(O)=O.[OH-].[Na+]>[Cu]I>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]([NH:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:8]3[C:9]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 14798Sodium HydroxideHCID 2733271Sodium methanesulfinateHCID 59375664HCID 59375664, compound

Product 1

HCID 59375399HCID 59375399, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

9-bromo-4-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (50 mg, 0.10 mmol), sodium methanesulfinate (13.27 mg, 0.130 mmol), DL-proline (2.302 mg, 0.020 mmol), copper(I) iodide (1.904 mg, 10.00=01) and NaOH (0.800 mg, 0.020 mmol) were combined in a 2-dram vial that was then flushed with nitrogen and kept under a nitrogen atmosphere. DMSO (500 μl) was then added and the reaction was heated to 90° C. and stirred for 72 h. Then, the reaction was purified by preparative HPLC reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to give the title compound as a pale yellow solid. LRMS (ESI) calc'd for (C19H23BrN3O3S) [M+H]+ 452.1; found 452.0.

Workup

  1. customwas then flushed with nitrogen
  2. additionDMSO (500 μl) was then added
  3. customThen, the reaction was purified by preparative HPLC reverse phase (C-18)
  4. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-d231c4a6e6694eb79beb394809072659
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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