Cesium carbonate → HCID 49858289, compound

HRID 1260556Notes

Reaction equation

HRID 1260556 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][N:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.CN(C)CC(O)=O>O1CCOCC1.[Cu](I)I>[CH:9]([O:8][C:5]1[N:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:17][CH:18]=2)=[N:3][CH:4]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 457877312-Bromo-5-[(propan-2-yl)oxy]pyrazineHCID 59956161N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

Product 1

HCID 49858289HCID 49858289, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-isopropoxypyrazine (100 mg, 0.46 mmol), N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide (143 mg, 0.69 mmol), cesium carbonate (300 mg, 0.92 mmol), copper iodide (8.77 mg, 0.046 mmol) and N,N-dimethylglycine hydrochloride (19.3 mg, 0.138 mmol) were stirred in 2 ml of dioxane at 100° C. under argon for 7 h. The batch was filtered, the filtrate was concentrated and admixed with ethyl acetate and water, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 88 mg (56%), M+H+: 344.16.

Workup

  1. filtrationThe batch was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe organic phase was separated off
  4. concentrationconcentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-5984310508844b98ab0738005d717b11
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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