Ethyl 2-(4-aminophenoxy)acetate → HCID 86724356, compound

HRID 1482704Notes

Reaction equation

HRID 1482704 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:24]=[C:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH:26]=[CH:27][CH:28]=2)[C:19]([F:34])=[CH:18][N:17]=1>C(O)CCC>[C:30]([NH:29][C:25]1[CH:24]=[C:23]([NH:22][C:20]2[C:19]([F:34])=[CH:18][N:17]=[C:16]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=3)[N:21]=2)[CH:28]=[CH:27][CH:26]=1)(=[O:33])[CH:31]=[CH2:32]

Participants

4

Reactant 2

HCID 412616Ethyl 2-(4-aminophenoxy)acetateHCID 86724332HCID 86724332, compound

Product 1

HCID 86724356HCID 86724356, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A solution of ethyl 2-(4-aminophenoxy)acetate (0.801 g) and N-(3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)acrylamide (1.0 g) in 1-butanol (10 mL) was heated to 135° C. for 2 hr. The reaction was monitored on TLC using hexanes:ethyl acetate (3:7) as mobile phase. After completion of the reaction, butanol was removed under reduced pressure and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried over sodium sulfate and solvent was removed under reduced pressure. Crude material was purified by Combiflash chromatography and eluted with 29% ethyl acetate in hexane to give 0.30 g of ethyl 2-(4-((4-((3-acrylamidophenyl)amino)-5-fluoropyrimidin-2-yl)amino)phenoxy)acetate.

Workup

  1. customwas removed under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over sodium sulfate and solvent
  5. customwas removed under reduced pressure
  6. customCrude material was purified by Combiflash chromatography
  7. washeluted with 29% ethyl acetate in hexane

Sources & evidence

ORD record
ord-097645cb725441a191fa597397a2082c
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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