Chloroform methanol → HCID 178511506, compound

HRID 1506171Notes

Reaction equation

HRID 1506171 reaction equation
[C:1]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OCC3C=CC=CC=3)[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.CO.C(Cl)(Cl)Cl>C(O)C.C(Cl)(Cl)Cl.[C].[Pd]>[C:1]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([NH2:19])[CH2:17][CH2:18]2)[N:2]=[N: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

6

Reactant 2

HCID 21584188Chloroform methanolHCID 178523580HCID 178523580, compound

Product 1

HCID 178511506HCID 178511506, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

5% Palladium-carbon (5.00 mg) was added to benzyl [trans-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]carbamate (7.00 mg, 0.0180 mmol) in a mixture of ethanol (1 mL) and chloroform (1 mL) under an argon atmosphere, and after the reaction system was flushed with hydrogen, the reaction mixture was stirred at room temperature for one day and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin layer chromatography (NH-PLC05 plate manufactured by Fuji Silysia Chemical Ltd.: methanol/chloroform=1/19 (v/v)) to give the title compound as a colorless solid (0.35 mg, yield 8.0%).

Workup

  1. customafter the reaction system was flushed with hydrogen
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel thin layer chromatography (NH-PLC05 plate

Sources & evidence

ORD record
ord-8a3a81d0fbbe4b5e90798334d4acfe06
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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