1,10-Phenanthroline → HCID 57721179, compound

HRID 1986393Notes

Reaction equation

HRID 1986393 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.N[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[N:26]1[C:39]2C(=CC=C3[C:38]=2[N:37]=[CH:36][CH:35]=C3)C=C[CH:27]=1.[C:40]([O-:43])([O-])=O.[Cs+].[Cs+].CO[CH2:48][CH2:49][O:50]C>C1(C)C=CC=CC=1.CO.[Cu]I.CS(C)=O>[CH2:11]([N:10]1[C:4]2[CH:3]=[C:2]([O:50][C:49]3[CH:20]=[CH:25][CH:24]=[C:23]([CH2:22][CH2:21][C:40]([N:37]4[CH2:38][CH2:39][N:26]([CH3:27])[CH2:35][CH2:36]4)=[O:43])[CH:48]=3)[N:7]=[CH:6][C:5]=2[N:8]=[C:9]1[C:13]1[C:14]([NH2:18])=[N:15][O:16][N:17]=1)[CH3:12]

Participants

10

Reactant 5

HCID 13181,10-PhenanthrolineHCID 6115AnilineHCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 160998514-(6-Bromo-1-Ethyl-1h-Imidazo[4,5-C]pyridin-2-Yl)-1,2,5-Oxadiazol-3-Amine

Product 1

HCID 57721179HCID 57721179, compoundYield 8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

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) (100 mg, 0.32 mmol) in toluene (5 mL) and DME (5 mL), was added the product of Step 1 (128 mg, 0.52 mmol), CuI (62 mg, 0.32 mmol), 1,10-phenanthroline (116 mg, 0.65 mmol), and Cs2CO3 (210 mg, 0.65 mmol). This mixture was then heated to 170° C. by microwave for 40 min. To the reaction mixture was added DMSO (2.0 mL), diluted with EtOAC/MeOH, sonicated for 10 min, then filtered and concentrated. 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 (12.0 mg, 8%). 1H NMR (400 MHz, MeOD) δ ppm 8.71 (d, 1H, 0.8 Hz), 7.35 (t, 1H, 8.0 Hz), 7.19 (d, 1H, 0.8 Hz), 7.10 (d, 1H, 7.6 Hz), 6.94-7.10 (m, 2H), 4.72 (q, 2H, 7.2 Hz), 3.42-3.61 (m, 4H), 2.96 (t, 2H, 7.6 Hz), 2.74 (t, 2H, 7.6 Hz), 2.40-2.48 (m, 4H), 2.35 (s, 3H), 1.46 (t, 3H, 7.2 Hz). MS (ES+) m/e 477 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-4ff01f37d27444dca4e7d78d84a4d7eb
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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