Water → HCID 60194099, compound

HRID 2171001Notes

Reaction equation

HRID 2171001 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[K+].O>O1CCOCC1>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[CH:3]=[C:2]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[CH:9][N:10]=2

Participants

6

Reactant 4

HCID 962WaterHCID 17274-AminopyridineHCID 23665647Potassium tert-butoxideHCID 68292787HCID 68292787, compound

Product 1

HCID 60194099HCID 60194099, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 52.2 mg (0.20 mmol) 8-chloro-6-(2-fluoro-phenyl)-pyrido[2,3-b]pyrazine in 1 ml dioxane was heated to 80° C. under nitrogen. Then 20.7 mg (0.22 mmol) 4-aminopyridine and 47.3 mg (0.42 mmol) potassium-tert-butoxide were added and the mixture was stirred at the same temperature for 5 minutes. Water was added to the reaction mixture. The resulting precipitate was filtered off and washed with water. The filtrate was extracted several times with dichloromethane; the organic phase was dried over sodium sulphate and evaporated. The residue was combined with the filtrate and purified by preparative HPLC. The fractions containing product were evaporated and partitioned between sodium hydrogen carbonate solution and dichloromethane. The organic phase was dried over sodium sulphate and evaporated yielding [6-(2-fluoro-phenyl)-pyrido[2,3-b]pyrazin-8-yl]-pyridin-4-yl-amine as yellow crystals HPLC/MS (A): 1.37 min, [M+H] 318.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with water
  3. extractionThe filtrate was extracted several times with dichloromethane
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customevaporated
  6. custompurified by preparative HPLC
  7. additionThe fractions containing product
  8. customwere evaporated
  9. custompartitioned between sodium hydrogen carbonate solution and dichloromethane
  10. dry with materialThe organic phase was dried over sodium sulphate
  11. customevaporated

Sources & evidence

ORD record
ord-b79350d4aae145fc98b3050487ca98b1
Source dataset
uspto-grants-2015_06
Patent number
US09051318B2

Reaction notes

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