7-(Benzyloxy)-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide → HCID 178425115, compound

HRID 79488Notes

Reaction equation

HRID 79488 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]2[C:15]([C:18]([NH:20][C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[C:23]([CH:38]3[CH2:40][CH2:39]3)=[N:24][N:25]4[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=3)=[O:19])=[CH:16][N:17]=[C:11]2[CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1>[CH:38]1([C:23]2[C:22]3[C:26](=[CH:27][CH:28]=[CH:29][C:21]=3[NH:20][C:18]([C:15]3[N:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]4=[N:17][CH:16]=3)=[O:19])[N:25]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=3)[N:24]=2)[CH2:40][CH2:39]1

Participants

5

Reactant 2

HCID 672596427-(Benzyloxy)-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 178425115HCID 178425115, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 7-(benzyloxy)-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.75 g, 1.4 mmol; prepared as in Example 157) and 10% Pd/C (Degussa type, 0.75 g, 0.35 mmol) was treated with THF (12 mL). The reaction vessel was heated at 55° C. with stirring while maintaining 100 psi of hydrogen in the headspace of the reaction vessel for 20 hours. The reaction mixture was cooled to ambient temperature and filtered to remove the catalyst. The filtrate was diluted with EtOAc (75 mL) and extracted with 2.5 N sodium hydroxide (2×50 mL). The pH of the combined aqueous extracts was adjusted to approximately 5 using 0.5 M monobasic potassium phosphate solution and 6 N HCl to induce precipitation. The resulting solid was collected by vacuum filtration and dried under vacuum to give the product (0.24 g). MS (ES+APCI) m/z=439.4 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. customto remove the catalyst
  4. additionThe filtrate was diluted with EtOAc (75 mL)
  5. extractionextracted with 2.5 N sodium hydroxide (2×50 mL)
  6. customprecipitation
  7. filtrationThe resulting solid was collected by vacuum filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-5028bd857ffe493b98e6e9345528e031
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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