HCID 59526054, compound → HCID 59525601, compound

HRID 385824Notes

Reaction equation

HRID 385824 reaction equation
C(OC(=O)[N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26]2[S:27][C:28]([C:34]3[C:39]([F:40])=[CH:38][C:37]([C:41]([OH:44])([CH3:43])[CH3:42])=[CH:36][C:35]=3[F:45])=[CH:29][C:30]=2[C:31]([NH2:33])=[O:32])[N:20]=1)[CH2:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:40][C:39]1[CH:38]=[C:37]([C:41]([OH:44])([CH3:43])[CH3:42])[CH:36]=[C:35]([F:45])[C:34]=1[C:28]1[S:27][C:26]([NH:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([CH2:18][NH:10][CH2:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])[N:20]=2)=[C:30]([C:31]([NH2:33])=[O:32])[CH:29]=1

Participants

5

Reactant 2

HCID 59526054HCID 59526054, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59525601HCID 59525601, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl{[6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}[2-(isopropylamino)-2-oxoethyl]carbamate (83 mg, 0.13 mmol) was dissolved in methanol. Palladium on carbon (0.68 mg, 6.4 μmol) was added and a hydrogen balloon was placed on top. The solution was evacuated and then charged with hydrogen several times. The reaction was stirred for 3 hours. The solution was filtered through celite and concentrated. The crude residue was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to yield the title compound.

Workup

  1. customThe solution was evacuated
  2. additioncharged with hydrogen several times
  3. filtrationThe solution was filtered through celite
  4. concentrationconcentrated
  5. customThe crude residue was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-1aa609a3954b4e4abbbe8bddd8b7ee0c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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