HCID 118046691, compound → HCID 118046609, compound

HRID 595870Notes

Reaction equation

HRID 595870 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[N:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 118046691HCID 118046691, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118046609HCID 118046609, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrazin-2-amine (645 mg, 2.77 mmol) in a round bottom flask that was flushed with argon was added Pd—C 10% degaussa (294 mg, 0.277 mmol). Then under argon with syringe was added MeOH (10 mL) and then last a hydrogen balloon was added. The flask was evacuated and refilled with hydrogen (6 X). The reaction was stirred at room temperature for total of 16 h, under the hydrogen balloon, followed by LCMS. The reaction was flushed with argon and 25 mL of DCM was added. The crude mixture was filtered through a Celite plug, and concentrated to constant mass to give 635 mg of the desired product as free base, used as is (98% yield). LCMS (m/z): 236.2 (MH+), 0.41 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.78 (d, J=1.2 Hz, 1H), 7.74 (d, J=1.2 Hz, 1H), 6.09 (s, 2H), 3.85 (s, 4H), 2.52-2.60 (m, 1H), 1.65-1.78 (m, 6H), 1.49-1.61 (m, 2H).

Workup

  1. additionwas added
  2. customThe flask was evacuated
  3. additionrefilled with hydrogen (6 X)
  4. customThe reaction was flushed with argon and 25 mL of DCM
  5. additionwas added
  6. filtrationThe crude mixture was filtered through a Celite plug
  7. concentrationconcentrated to constant mass

Sources & evidence

ORD record
ord-2e049137120f48f9811de62155bc7bcd
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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