Cyanoacetic acid → HCID 71264155, compound

HRID 1506165Notes

Reaction equation

HRID 1506165 reaction equation
[C:1]1([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21]CC3C=CC=CC=3)=O)[CH2:14]2)[N:2]=[CH:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.[C:29]([CH2:31]C(O)=O)#[N:30].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(O)C.[OH-].[Pd+2].[OH-].[C].C(Cl)(Cl)Cl.CO.O>[C:1]1([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:21])[CH2:31][C:29]#[N:30])[CH2:14]2)[N:2]=[CH:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2

Participants

9

Reactant 4

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70983629HCID 70983629, compound

Product 1

HCID 71264155HCID 71264155, compoundYield 11%

Reagents, catalysts & solvents 4

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

Benzyl 3-(7H-imidazo[1,5-c]pyrrolo[3,2-e]pyrimidin-1-yl)piperidine-1-carboxylate (13.3 mg, 0.0354 mmol) and 10% palladium hydroxide-carbon (small amount) in ethanol (1.5 mL) was stirred at room temperature for 2.5 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (1 mL) and stirred with 2-cyanoacetic acid (5.0 mg, 0.054 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (27.5 mg, 0.0722 mmol) and N,N-diisopropylethylamine (19.0 μL, 0.11 mmol) at room temperature for one day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography (NH-PLC05 plate manufactured by Fuji Silysia Chemical Ltd.: chloroform/methanol=15/1 (v/v)) to give the title compound as a pale yellow oil (1.02 mg, yield 11%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in N,N-dimethylformamide (1 mL)
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel thin layer chromatography (NH-PLC05 plate

Sources & evidence

ORD record
ord-5943ad360c96424c978dd62d79413d38
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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