Potassium Phosphate, Tribasic → HCID 59636151, compound

HRID 80247Notes

Reaction equation

HRID 80247 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.[CH2:16]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1Br)[CH3:17].CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:16]([O:18][C:19](=[O:27])[C:20]1[CH:21]=[CH:22][N:23]=[CH:24][C:25]=1[N:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)[C:11]1=[O:15])[CH3:17]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 15141565Ethyl 3-bromoisonicotinateHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 59636151HCID 59636151, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 0.25 g, 1.1 mmol) was reacted with 3-bromo-isonicotinic acid ethyl ester (0.28 g, 1.2 mmol), 1,4-dioxane (30 mL), copper iodide (0.065 g, 0.3 mmol), trans N,N′-dimethyl-cyclohexane-1,2-diamine (0.048 g, 0.3 mmol) and potassium phosphate (0.81 g, 2.8 mmol) to afford the crude product. Purification by column chromatography on silica gel (100% CHCl3) afforded 160 mg of the product (38.2% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (100% CHCl3)

Sources & evidence

ORD record
ord-306cc208c9d840c2b57559d41001d37d
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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