1,4-Dioxane → 1-Benzothiazol-6-yl-3-(4-pyrrolidin-1-ylmethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80235

Reaction equation

HRID 80235 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.CNC1C[CH2:22][CH2:21][CH2:20][CH:19]1[NH:24][CH3:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:39][CH2:38]OCC1>C(Cl)Cl.[Cu](I)I.CO>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:5]4[CH:4]=[N:3][CH:2]=[CH:38][C:39]=4[CH2:25][N:24]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 498726511-Benzothiazol-6-yl-3-(4-pyrrolidin-1-ylmethyl-pyridin-3-yl)-imidazolidin-2-oneYield 18.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Using the same reaction conditions and work up as described in Example 1, step -3,3-bromo-4-pyrrolidin-1-ylmethyl-pyridine (I-176a: 290 mg, 1.205 mmol) was refluxed with 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 220 mg, 1.004 mmol), copper iodide (19 mg, 0.1004 mmol), N,N′-Dimethyl-cyclohexane-1,2-diamine (42.7 mg, 0.301 mmol), potassium phosphate (640 mg, 3.012 mmol) and 1,4-dioxane (15 mL) at 120° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (5% MeOH in DCM). Purification by column chromatography on silica gel (5% MeOH in chloroform) followed by preparative HPLC afforded 72 mg of the product (18.9% yield).

Workup

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (5% MeOH in chloroform)

Sources & evidence

ORD record
ord-3096c593b7704a7dbfc86954866657e1
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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