Pyridine → HCID 70323530, compound

HRID 1868467Notes

Reaction equation

HRID 1868467 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:7]2[CH:30]=1)(=O)[NH2:2].N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>O1CCOCC1>[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:7]2[CH:30]=1)#[N:2]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 9845Trifluoroacetic anhydride2×HCID 86606998HCID 86606998, compound

Product 1

HCID 70323530HCID 70323530, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl (2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (Example 58, Step 2, 30 mg, 0.07 mmol) in dioxane (1.5 mL) was added pyridine (10.5 mg, 0.13 mmol) and TFAA (15.4 mg, 0.07 mmol). The reaction was kept at room temperature for 16 and additional pyridine (10.5 mg, 0.13 mmol) and TFAA (15.4 mg, 0.07 mmol) were added. After 5 h, the reaction was quenched by H2O and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl (2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (20 mg, 69% yield).

Workup

  1. additionwere added
  2. customthe reaction was quenched by H2O
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with satd aq NH4Cl and brine
  5. dry with materialto drying over MgSO4
  6. filtrationFiltration, concentration
  7. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-9eae1712bd8b4621b5378c6e179cc996
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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