HCID 90113976, compound → HCID 76071939, compound

HRID 2275871Notes

Reaction equation

HRID 2275871 reaction equation
[N:1]([CH2:4][CH:5]([NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])[C:17]2=[N:16][C:15]=1[CH3:33])=[O:13])[CH2:6][C:7]([F:10])([F:9])[F:8])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][CH2:4][CH:5]([NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])[C:17]2=[N:16][C:15]=1[CH3:33])=[O:13])[CH2:6][C:7]([F:8])([F:10])[F:9]

Participants

5

Reactant 2

HCID 90113976HCID 90113976, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 76071939HCID 76071939, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

555 mg of rac-N-(1-azido-4,4,4-trifluorobutan-2-yl)-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide (Example 41A, 1.19 mmol) were initially charged in 74 ml of ethanol, 126 mg of palladium on activated carbon (10%) were added and the mixture was hydrogenated at hydrogen standard pressure and RT for 60 min. The reaction solution was filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product-containing fractions were taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated. This gave 473 mg of the title compound (88% of theory).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8091e032c47c4da5912b75c99a85a326
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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