1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58115049, compound

HRID 1808697Notes

Reaction equation

HRID 1808697 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]#[C:10][C:11]1[N:12]=[C:13]2[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2=[N:15][CH:16]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O.[Cu](I)I>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:12]2[C:11]([CH:16]=[N:15][C:14]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:25])[CH3:26])[CH:18]=[CH:19][C:13]=32)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58115030HCID 58115030, compound

Product 1

HCID 58115049HCID 58115049, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a flask containing (+/−)-2-[3-(2-methyl-piperidin-1-yl)-prop-1-ynyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (185 mg, 0.48 mmol) was added copper iodide (37 mg, 0.19 mmol), and DBU (0.34 mL, 2.28 mmol) in dry dimethyl acetamide (1 mL). The mixture was vacuum degassed and heated to 130° C. and stirred for 3 hours. The mixture was cooled to ambient and quenched via the addition of water (30 ml) and ethyl acetate (30 ml).The material was shaken in a reparatory funnel, and the ethyl acetate phase was collected. The aqueous phases were back extracted with ethyl acetate (2×25 ml), the organics combined, dried (MgSO4), filtered and stripped. The remainder was purified by preparative TLC using 25% ethyl acetate in hexanes as eluant. The product band was collected to provide 36 mg of (+/−)-8-(2-methyl-piperidin-1-yl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-3,4,8a-triaza-as-indacene as a brown-black oil. Note that starting material (90 mg) was also recovered. This material was subjected to the identical reaction conditions as above (but over-night heating), to provide an extra 12 mg of product. MS (M+H)+=385.

Workup

  1. customdegassed
  2. temperatureThe mixture was cooled to ambient and
  3. customquenched via the addition of water (30 ml) and ethyl acetate (30 ml).The material
  4. stirringwas shaken in a reparatory funnel
  5. customthe ethyl acetate phase was collected
  6. extractionThe aqueous phases were back extracted with ethyl acetate (2×25 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe remainder was purified by preparative TLC
  10. customThe product band was collected

Sources & evidence

ORD record
ord-ac7672c3079343e9a2c2f2a37335165d
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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