Methanol → HCID 59596980, compound

HRID 2066190Notes

Reaction equation

HRID 2066190 reaction equation
C([O:8][C:9]([C:11]1([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]([CH3:41])[CH:34]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]4)=[O:32])[CH:25]=3)=[CH:19][C:18]=2[F:42])=[O:15])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.CO>O1CCCC1.[OH-].[OH-].[Pd+2]>[F:42][C:18]1[CH:19]=[C:20]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]([CH3:41])[CH:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[O:32])[CH:25]=2)[CH:21]=[CH:22][C:17]=1[NH:16][C:14]([C:11]1([C:9]([OH:10])=[O:8])[CH2:13][CH2:12]1)=[O:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 59596925HCID 59596925, compound

Product 1

HCID 59596980HCID 59596980, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(benzyloxycarbonyl)-N-(2-fluoro-4-{2-[3-methyl-3-(1-methylpiperidin-4-yl)ureido]pyridin-4-yloxy}phenyl)cyclopropanecarboxamide (510 mg) in tetrahydrofuran (20 ml)-methanol (20 ml) was added 20% palladium hydroxide on carbon (377 mg), followed by stirring under a hydrogen atmosphere at room temperature for 24 hr. The catalyst was removed by filtration, and washed with tetrahydrofuran-methanol (1:1). The filtrate was concentrated under reduced pressure, and the residue was dried under reduced pressure to provide the titled compound as white crystals (358.7 mg, 83%).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with tetrahydrofuran-methanol (1:1)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-574a487ee4d04298a496f056647ba409
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

Loading…