Tetrahydrofuran → HCID 57677757, compound

HRID 492907Notes

Reaction equation

HRID 492907 reaction equation
O1CCCC1.[F:6][C:7]1[CH:35]=[C:34]([N+:36]([O-])=O)[CH:33]=[CH:32][C:8]=1[O:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:21][CH2:20]2)=[O:18])[CH:11]=1.[H][H]>[C].[Pd].CO>[NH2:36][C:34]1[CH:33]=[CH:32][C:8]([O:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:21][CH2:20]3)=[O:18])[CH:11]=2)=[C:7]([F:6])[CH:35]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 57677559HCID 57677559, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57677757HCID 57677757, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

After adding tetrahydrofuran (3 ml) and methanol (3 ml) to a crude product of 4-[2-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide (129 mg) under a nitrogen atmosphere, 10% palladium-carbon (60 mg) was added, the atmosphere in the reaction vessel was replaced with hydrogen, and the mixture was stirred for 4.5 hours. The atmosphere in the reaction vessel was then replaced with nitrogen, and the catalyst was filtered and washed with methanol. The filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=19:1), and then Fractions containing the target compound were concentrated under reduced pressure to provide a crude product of the title compound (98.4 mg) as a pale yellow amorphous substance.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=19:1)
  5. additionFractions containing the target compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-87edeb10ffce4e22bc8575c18d3468b4
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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