HCID 86717972, compound → HCID 86717971, compound

HRID 2275889Notes

Reaction equation

HRID 2275889 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][CH:19]([CH3:33])[C@H:20]([NH:22]C(=O)OCC3C=CC=CC=3)[CH3:21])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1>C(O)C.[Pd]>[NH2:22][C@H:20]([CH3:21])[CH:19]([NH:18][C:16]([C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[C:2]([F:1])=[CH:37][CH:36]=[CH:35][C:34]=3[F:38])[C:7]2=[N:14][C:13]=1[CH3:15])=[O:17])[CH3:33]

Participants

4

Reactant 1

HCID 86717972HCID 86717972, compound

Product 1

HCID 86717971HCID 86717971, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

235 mg of benzyl {(2R)-3-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]butan-2-yl}carbamate (Example 184A, 0.45 mmol, 1 equivalent) were dissolved in 260 ml of ethanol, and 63 mg of palladium on activated carbon (10%, 0.45 mmol, 1 equivalent) were added. The mixture was hydrogenated at RT under atmospheric pressure for 1.5 h and then filtered through silica gel and concentrated. The residue was dissolved in methanol and purified by preparative HPLC (Method 9). This gave 96 mg (55% of theory) of the title compound.

Workup

  1. filtrationfiltered through silica gel
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified by preparative HPLC (Method 9)

Sources & evidence

ORD record
ord-0efbc7424aa04fc6aa46a849e1879fcc
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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