HCID 59850189, compound → HCID 59850175, compound

HRID 2064130Notes

Reaction equation

HRID 2064130 reaction equation
[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[CH:4][C:5](I)=[C:6]([NH:8][C:9]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[O:10])[CH:7]=1>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd+2].O1CCOCC1>[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[CH:4][C:5]2[N:11]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:9](=[O:10])[NH:8][C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 59850189HCID 59850189, compound

Product 1

HCID 59850175HCID 59850175, compound

Reagents, catalysts & solvents 2

HCID 178478645Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, dry 1,4-dioxane (5 ml), palladium 1,1′-bis(diphenyl-phosphino)ferrocene dichloride (10% mol, 0.268 mmol, 220 mg), NatBuO (2 eq., 5.36 mmol, 520 mg) were mixed together and sonicated at room temperature for 10 minutes; 1,1-dimethylethyl 4-[({[5-chloro-2-iodo-4-(trifluoromethyl)phenyl]amino}carbonyl)amino]-1-piperidinecarboxylate D11 (2.68 mmol, 1.5 g) was then added at room temperature and the mixture was heated to 80° C. overnight. The reaction mixture was cooled to room temperature, quenched with NH4Cl (saturated solution) and the aqueous solution obtained was extracted with ethyl acetate; the organics were combined, dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound that was purified by chromatography (methanol-NH3-dichloromethane) to yield the title compound, 115 mg, 10%, M+−H=418.

Workup

  1. customsonicated at room temperature for 10 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with NH4Cl (saturated solution)
  4. customthe aqueous solution obtained
  5. extractionwas extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto afford the crude compound that
  10. customwas purified by chromatography (methanol-NH3-dichloromethane)

Sources & evidence

ORD record
ord-0dbd2ea529914a598bd3c8be969fa943
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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