Dimethylformamide → HCID 59170863, compound

HRID 1362627Notes

Reaction equation

HRID 1362627 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:8]=[C:9](/[CH:18]=[CH:19]/[C:20]([OH:22])=O)[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[NH2:23][CH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.O>[F:6][C:7]1[CH:8]=[C:9](/[CH:18]=[CH:19]/[C:20]([NH:23][CH:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)=[O:22])[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 123445(+-)-1-AminoindanHCID 2724699PyBOPHCID 29019163(2E)-3-[3-Fluoro-4-(1H-imidazol-1-yl)phenyl]-2-propenoic acid

Product 1

HCID 59170863HCID 59170863, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (4.0 mL) solution of (E)-3-[3-fluoro-4-(1H-imidazol-1-yl)phenyl]acrylic acid (100 mg), TEA (167 μL), 1-aminoindane (83.0 μL) and PYBOP (448 mg) were added one by one, and the reaction solution was agitated at room temperature overnight. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=1:1→ethyl acetate), and 95.0 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. additionwere added to the reaction solution
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-fcba7d2e4d184999802dea61b8b45636
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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