Pyrazole → HCID 44554075, compound

HRID 1254051Notes

Reaction equation

HRID 1254051 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.N1C=CC=N1.C[NH:34][CH2:35][CH2:36][NH:37][CH3:38].CC(C)([O-])C.[K+]>[Cu]I.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([N:34]3[CH:35]=[CH:36][N:37]=[CH:38]3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8070N,N'-DimethylethylenediamineHCID 23665647Potassium tert-butoxideHCID 44554077HCID 44554077, compound

Product 1

HCID 44554075HCID 44554075, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave tube were added 2-[5-[(4-chlorophenyl)thio]-4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl]pyridine (Example 61, 150 mg, 0.30 mmol), CuI (57 mg, 0.30 mmol), pyrazole (61 mg, 0.89 mmol), N,N′-dimethylethylenediamine ((79 mg, 0.89 mmol), potassium t-butoxide (100 mg, 0.89 mmol), and 4 mL of NMP. The reaction was heated at 150° C. for 90 min via microwave. After filtration through Celite, the reaction mixture was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.65 (d, 1H), 8.37 (d, 1H), 8.24 (d, 2H), 7.98 (broad s, 1H), 7.84 (t, 1H), 7.43 (d, 2H), 7.36 (t, 1H), 7.25 (d, 2H), 7.04 (d, 2H), 4.15 (s, 3H). LCMS: m/z 444 (M+H)+.

Workup

  1. filtrationAfter filtration through Celite
  2. customthe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-398deea36c4d4e56a8733acb80faf1cc
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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