HCID 136341325, compound → HCID 178511075, compound

HRID 1506184Notes

Reaction equation

HRID 1506184 reaction equation
[C:1]1([CH:13]2[CH2:18][CH2:17][C:16](=[CH:19][C:20]#[N:21])[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>O1CCCC1.[C].[Pd]>[C:1]1([C@@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][C:20]#[N:21])[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.[C:1]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][C:20]#[N:21])[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

5

Reactant 1

HCID 136341325HCID 136341325, compound

Product 2

HCID 178511074HCID 178511074, compoundYield 6%HCID 178511075HCID 178511075, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexylidene]acetonitrile (20.0 mg, 0.0720 mmol) in tetrahydrofuran (10 mL) were stirred with 5% palladium-carbon (10 mg) at room temperature for 4 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography (hexane/ethyl acetate=1/1 (v/v)) to give 2-[cis-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]acetonitrile (Synthetic Examplea 435a; colorless solid, 1.30 mg, yield 6%) in a less polar fraction and 2-[trans-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]acetonitrile (Synthetic Examplea 435b; colorless solid, 3.40 mg, yield 17%) in a more polar fraction.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel thin layer chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-d348fcea817d4896a48267d5d138316f
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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