Tetrahydrofuran → HCID 23153214, compound

HRID 492882Notes

Reaction equation

HRID 492882 reaction equation
O1CCCC1.[F:6][C:7]1[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][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][CH:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]2)=[O:18])[CH:11]=1.[H][H]>[C].[Pd].CO>[NH2:33][C:31]1[CH:30]=[CH:29][C:8]([O:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([N:19]3[CH2:20][CH2:21][CH:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:23][CH2:24]3)=[O:18])[CH:11]=2)=[C:7]([F:6])[CH:32]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23153349HCID 23153349, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23153214HCID 23153214, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

After adding tetrahydrofuran (2 ml) and methanol (2 ml) to 4-(dimethylaminomethyl)piperidine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide (88 mg) under a nitrogen atmosphere, 10% palladium-carbon (45 mg) was added, the atmosphere in the reaction vessel was replaced with hydrogen, and the mixture was stirred for 9 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 to provide a crude product of 4-(dimethylaminomethyl)piperidine-1-carboxylic acid [6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]amide (90 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

Sources & evidence

ORD record
ord-4465ccda754646d48c0ff9362e824ad3
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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