Potassium Phosphate, Tribasic → 1-Benzothiazol-6-yl-3-imidazo[1,2-a]pyrazin-5-yl-imidazolidin-2-one

HRID 80250Notes

Reaction equation

HRID 80250 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Cl[C:17]1[N:22]2[CH:23]=[CH:24][N:25]=[C:21]2[CH:20]=[N:19][CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[N:22]5[CH:23]=[CH:24][N:25]=[C:21]5[CH:20]=[N:19][CH:18]=4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 128415885-Chloroimidazo[1,2-A]pyrazineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 498727461-Benzothiazol-6-yl-3-imidazo[1,2-a]pyrazin-5-yl-imidazolidin-2-oneYield 3.53%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 240 mg, 1.0945 mmol) was reacted with 5-chloro-imidazo[1,2-a]pyrazine (I-186a: 202 mg, 1.3135 mmol), 1,4-dioxane (3 mL), copper iodide (24 mg), trans N,N′-dimethyl-cyclohexane-1,2-diamine (48 mg) and potassium phosphate (581 mg, 2.7364 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by preparative HPLC afforded 13 mg of the product (3.53% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-879dd618d5074e5eb107c8aaf858377f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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