Imidazole → HCID 58102289, compound

HRID 1046817Notes

Reaction equation

HRID 1046817 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:10])=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.N1C=CN=C1.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[O:22][C:23]1[CH:24]=[C:25]([C:32](O)=[O:33])[C:26](=[CH:30][CH:31]=1)[C:27](O)=[O:28].O>CN(C=O)C.C(OCC)(=O)C>[NH2:9][C:5]1[C:4]([F:10])=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:1]1[C:32](=[O:33])[C:25]2[C:26](=[CH:30][CH:31]=[C:23]([O:22][C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:16]=3)[CH:24]=2)[C:27]1=[O:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 55285672HCID 55285672, compoundHCID 59139455HCID 59139455, compound

Product 1

HCID 58102289HCID 58102289, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

3-Aminomethyl-2-fluoro-phenylamine (50.8 mg, 0.362 mmol) and imidazole (26.0 mg, 0.382 mmol) were added to a solution of 4-(pyrimidin-2-yloxy)phthalic acid (94.1 mg, 0.362 mmol) in DMF (2.0 mL), and the mixture was stirred in a Microwave at 300 W, 150° C. for 5 minutes. Water was then added to the reaction mixture, extraction was performed with ethyl acetate, and the organic extract was washed with saturated saline. After drying over magnesium sulfate, it was concentrated under reduced pressure to yield a crude product, which was then purified by column chromatography to yield the title compound (13.4 mg, 10%) as a white solid.

Workup

  1. extractionthe organic extract
  2. washwas washed with saturated saline
  3. dry with materialAfter drying over magnesium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customto yield a crude product, which
  6. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-78839c4d100345e497162658f7de076b
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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