HCID 73055080, compound → HCID 73055362, compound

HRID 1052246Notes

Reaction equation

HRID 1052246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]4[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH:27]=4)[NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>CO.[Pd]>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([CH:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[NH:19][C:16]3=[N:17][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 73055080HCID 73055080, compound

Product 1

HCID 73055362HCID 73055362, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine (from Example 23, 10 mg, 26.4 μmol) in methanol (1 mL), Pd/C (10% w/w, 3.2 mg, 3.0 μmol) was added. The reaction mixture was then stirred under the atmosphere of H2 at ambient temperature. After 3 hours, the palladium catalyst was filtered and the crude mixture was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (3.0 mg, 30%) as its TFA salt. LCMS calculated for C22H29N4O2 (M+H)+: m/z=381.2. Found: 381.3.

Workup

  1. filtrationthe palladium catalyst was filtered
  2. customthe crude mixture was purified on RP-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-6e0f1b90c2064af3ac62375771eb0f4f
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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