1,10-Phenanthroline → HCID 68873842, compound

HRID 1986396Notes

Reaction equation

HRID 1986396 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)[N:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1.NC1C=CC=CC=1.[OH:26][C:27]1[CH:28]=[C:29]([C:33](=[O:44])[CH:34]([CH3:43])[CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:30]=[CH:31][CH:32]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.COCCOC.CO.[Cu]I.CS(C)=O>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:4]3[CH:3]=[C:2]([O:26][C:27]4[CH:28]=[C:29]([C:33](=[O:44])[CH:34]([CH3:43])[CH2:35][CH2:36][N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)[CH:30]=[CH:31][CH:32]=4)[N:7]=[CH:6][C:5]=3[N:8]=2)=[N:17][O:16][N:15]=1

Participants

11

Reactant 5

HCID 13181,10-PhenanthrolineHCID 6115AnilineHCID 10796Cesium carbonateHCID 160998514-(6-Bromo-1-Ethyl-1h-Imidazo[4,5-C]pyridin-2-Yl)-1,2,5-Oxadiazol-3-AmineHCID 68870181HCID 68870181, compound

Product 1

HCID 68873842HCID 68873842, compoundYield 46%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
170 °C

Procedure

Under argon, to a suspension of 4-(6-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-furazan-3-amine (prepared by the method of Example 8, Steps 3-7, substituting ethylamine for aniline in Step 3) (80 mg, 0.26 mmol) in toluene (4 mL) and DME (4 mL), was added the product of Step 2 (88 mg, 0.31 mmol), CuI (50 mg, 0.26 mmol), 1,10-phenanthroline (94 mg, 0.52 mmol), and Cs2CO3 (170 mg, 0.52 mmol). This mixture was then heated to 170° C. by microwave for 15 min. To the reaction mixture was added DMSO (2.0 mL), diluted with EtOAC/MeOH, sonicated for 10 min, then filtered and concentrated. The residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA), to afford the title compound as a pale yellow solid (72.0 mg, 46%). 1H NMR (400 MHz, DMSO) δ ppm 9.71 (bs, 1H), 8.77 (d, 1H, 0.8 Hz), 7.84 (d, 1H, 8.0 Hz), 7.69 (t, 1H, 2 Hz), 7.59-7.64 (m, 2H), 7.45 (dd, 1H, 8 Hz, 0.8 Hz), 6.96 (s, 2H), 4.70 (q, 2H, 7.2 Hz), 3.98 (d, 2H, 12.4 Hz), 3.60-3.81 (m, 2H), 3.42-3.47 (m, 2H), 3.01-3.19 (m, 4H), 1.96-2.01 (m, 1H), 1.41 (t, 3H, 7.2 Hz), 1.38 (d, 3H, 10.4 Hz). MS (ES+) m/e 492 [M+H]+.

Workup

  1. customprepared by the method of Example 8, Steps 3-7
  2. customsonicated for 10 min
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA)

Sources & evidence

ORD record
ord-71c24faebfd647a6a36845bdf3439df2
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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