Ethanol → 4-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-3-fluorophenoxy)pyridin-2-yl]amide

HRID 492765Notes

Reaction equation

HRID 492765 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:29]C(=O)OCC1C=CC=CC=1.C(O)C>O1CCCC1.[C].[Pd]>[NH2:29][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 702EthanolHCID 23153372Benzyl (2-fluoro-4-{2-[(4-pyrrolidin-1-ylpiperidine-1-carbonyl)amino]pyridin-4-yloxy}phenyl)carbamate

Product 1

HCID 576775624-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-3-fluorophenoxy)pyridin-2-yl]amide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2-fluoro-4-{2-[(4-pyrrolidin-1-ylpiperidine-1-carbonyl)amino]pyridin-4-yloxy}phenyl)carbamate (91 mg) in tetrahydrofuran (10 ml) was 10% palladium carbon (36.4 mg), followed by stirring under a hydrogen atmosphere at room temperature for 3.5 hrs. Ethanol (5.0 ml) was added thereto, followed by stirring under a hydrogen atmosphere at room temperature for 1.5 hrs. The reaction mixture was filtered to remove the catalyst, and washed with a small amount of tetrahydrofuran to give a solution of the titled compound in tetrahydrofuran. The solution was concentrated to almost dryness, which was then used for succeeding reactions without further purification.

Workup

  1. stirringby stirring under a hydrogen atmosphere at room temperature for 1.5 hrs
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. washwashed with a small amount of tetrahydrofuran

Sources & evidence

ORD record
ord-d328efae730e477e80b89b62ebb6af30
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…