HCID 57677643, compound → HCID 57677632, compound

HRID 492848Notes

Reaction equation

HRID 492848 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:23][CH2:22][CH2:21]3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>CO.[C].[Pd]>[NH2:28][C:26]1[CH:25]=[CH:24][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[CH2:23][CH2:22][CH2:21]4)[CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:27]=1

Participants

4

Reactant 1

HCID 57677643HCID 57677643, compound

Product 1

HCID 57677632HCID 57677632, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

After adding 10% palladium-carbon (85 mg) to a solution of 4-(azetidin-1-yl)piperidine-1-carboxylic acid (6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl)amide (364 mg) in methanol (20 ml), the mixture was stirred for 12 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered and the filtrate was concentrated under reduced pressure. The obtained solid was suspended in ethyl acetate and diluted with diethyl ether. The solid was filtered and washed with diethyl ether. It was then subjected to aeration drying to provide the title compound (160 mg) as white powder.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additiondiluted with diethyl ether
  4. filtrationThe solid was filtered
  5. washwashed with diethyl ether
  6. customdrying

Sources & evidence

ORD record
ord-4aa326e1f9484ac2bbd3c34e972c7246
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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