HCID 90135971, compound → HCID 90114075, compound

HRID 2275880Notes

Reaction equation

HRID 2275880 reaction equation
[F:1][C:2]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][CH:19]([CH2:32][O:33][CH:34]([CH3:36])[CH3:35])[CH2:20][NH:21]C(=O)OCC3C=CC=CC=3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1>C(O)C.[Pd]>[NH2:21][CH2:20][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:37]([F:41])=[CH:38][CH:39]=[CH:40][C:2]=3[F:1])[C:7]2=[N:14][C:13]=1[CH3:15])=[O:17])[CH2:32][O:33][CH:34]([CH3:36])[CH3:35]

Participants

4

Reactant 1

HCID 90135971HCID 90135971, compound2×

Product 1

HCID 90114075HCID 90114075, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

305 mg of rac-benzyl {2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]-3-isopropoxypropyl}carbamate (intermediate 116A; 0.54 mmol) were initially charged in 46 ml of ethanol, 44 mg of 10% palladium on activated carbon were added and the mixture was hydrogenated under hydrogen standard pressure for 4 hours. The reaction mixture was filtered and concentrated and the residue was purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur 100-5 C18 HTEC, 50×21 mm; mobile phase: gradient with 0.1% strength aqueous ammonia solution and methanol). This gave 127 mg of the title compound (54% of theory).

Workup

  1. customfor 4 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur 100-5 C18 HTEC, 50×21 mm; mobile phase: gradient with 0.1% strength aqueous ammonia solution and methanol)

Sources & evidence

ORD record
ord-16d52e00a4de4d54bf25abbe07314cc3
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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