Cesium carbonate → HCID 58608133, compound

HRID 2243570Notes

Reaction equation

HRID 2243570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[O:23][C:24]([C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=4)=[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]=23)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH:40]([N:43]([CH:47]([CH3:49])[CH3:48])[CH2:44][CH2:45]Cl)([CH3:42])[CH3:41].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[O:23][C:24]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH2:45][CH2:44][N:43]([CH:47]([CH3:49])[CH3:48])[CH:40]([CH3:42])[CH3:41])=[CH:34][CH:33]=4)=[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]=23)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 58608109HCID 58608109, compound

Product 1

HCID 58608133HCID 58608133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A resealable tube was charged with 4-{2-[2-(4-hydroxy-phenyl)-3-phenyl-furo[2,3-b]pyridin-4-ylamino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester 8a (0.070 g, 0.136 mmol), 2-diisopropylaminoethylchloride hydrochloride 9a (0.029 g, 0.143 mmol), cesium carbonate (0.222 g, 0.680 mmol), and DMF (2.0 mL). The system was purged with argon and the tube was sealed. The mixture stirred at 85° C. for 17 h. The reaction mixture was then partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a green oil. This oil was purified via preparative thin layer chromatography (eluting with 95:5:0.5, dichloromethane/methanol, ammonium hydroxide) to afford 4-(2-{2-[4-(2-diisopropylamino-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridin-4-ylamino}-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 10a as a yellow oil. MS (MH+) 642.4; Calculated 641 for C38H51N5O4.

Workup

  1. customThe system was purged with argon
  2. customthe tube was sealed
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a green oil
  11. customThis oil was purified via preparative thin layer chromatography (eluting with 95:5:0.5, dichloromethane/methanol, ammonium hydroxide)

Sources & evidence

ORD record
ord-a500f3e11aba4bceb5e32167148f1142
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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