Potassium Carbonate → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(piperidin-1-ylcarbonyl)furo[2,3-b]pyridin-3-amine

HRID 8787Notes

Reaction equation

HRID 8787 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:24]([NH:25]C(=O)C(F)(F)F)=[C:23]([C:32]([N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:33])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:24]([NH2:25])=[C:23]([C:32]([N:34]4[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]4)=[O:33])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 10483669N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(piperidin-1-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-2,2,2-trifluoroacetamide

Product 1

HCID 103912875-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(piperidin-1-ylcarbonyl)furo[2,3-b]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 35 mg of the product of Example 12 dissolved in 1 mL of methanol was treated with 41 mg of K2CO3 at 60° C. for 2 hours. The reaction mixture was then partitioned between EtOAc and water and the organic product was extracted. The extracts were dried (Na2SO4), filtered and evaporated in vacuo to afford to afford the title compound. HPLC/MS: 500.1 (M+1), 502.1 (M+3); Rt=4.51 min.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and water
  2. extractionthe organic product was extracted
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford

Sources & evidence

ORD record
ord-cb04649c7f1948398453cc6289ed3098
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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