HCID 59252416, compound → HCID 59252390, compound

HRID 2274483Notes

Reaction equation

HRID 2274483 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[NH:17][C:16](/[CH:18]=[CH:19]/[C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[N:15][CH:14]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]([CH2:18][CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[N:15][CH:14]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59252416HCID 59252416, compound

Product 1

HCID 59252390HCID 59252390, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared by subjecting (E)-2-phenyl-5-(2-(2-(pyridin-3-yl)vinyl)-1H-imidazol-5-yl)pyrimidine (Example 15, 7 mg, 0.02 mmol) to hydrogenation using 10% palladium on carbon (dry, 1 mg) in ethanol (3 mL). After five days, the reaction mixture was filtered through Celite using ethanol to rinse. Evaporation provided the title compound as a brown solid (7 mg, quantitative yield); melting point 113° C.; 1H-NMR (400 MHz; CD3OD) δ 9.16 (s, 2H), 8.39-8.44 (m, 4H), 7.64 (s, 1H), 7.52-7.53 (m, 5H)), 3.12-3.19 (m, 4H); LC/MS (ESI+) m/z 328; H-PGDS FPBA IC50: 0.3 μM.

Workup

  1. customThe title compound was prepared
  2. filtrationthe reaction mixture was filtered through Celite
  3. washto rinse
  4. customEvaporation

Sources & evidence

ORD record
ord-4438a46b0c5c4e3ab84798b16e954ae9
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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