Hexane → 4-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

HRID 492747Notes

Reaction equation

HRID 492747 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].CCCCCC>O1CCCC1.CO.C(OCC)C.[C].[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 8058HexaneHCID 57677470HCID 57677470, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 231532634-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridineYield 90.8%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine-1-carboxylic acid [4-(4nitrophenoxy)pyridin-2-yl]amide (636 mg) was dissolved in tetrahydrofuran (18 ml)-methanol (18 ml), and then 10% palladium carbon (412 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with methanol. The filtrate was concentrated under a reduced pressure to give a residue, which was suspended in diethyl ether (10 ml)-hexane (10 ml). The solid was filtered off, and dried in vacuum to provide the titled compound (524.9 mg, 90.7%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with methanol
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue, which
  6. filtrationThe solid was filtered off
  7. customdried in vacuum

Sources & evidence

ORD record
ord-680a078a2ac141888f14a758d57f7415
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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