HCID 118598959, compound → HCID 118598868, compound

HRID 1050340Notes

Reaction equation

HRID 1050340 reaction equation
[CH3:1][C:2]1([CH3:22])[N:6]2[C:7](=[O:20])[C:8]([N:11]3[C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:14]=4[CH:13]=[CH:12]3)=[CH:9][CH:10]=[C:5]2[C:4](=[O:21])[NH:3]1.[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH3:22])[N:6]2[C:7](=[O:20])[C:8]([N:11]3[C:15]4[N:16]=[CH:17][N:18]=[CH:19][C:14]=4[CH2:13][CH2:12]3)=[CH:9][CH:10]=[C:5]2[C:4](=[O:21])[NH:3]1

Participants

5

Reactant 2

HCID 118598959HCID 118598959, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118598868HCID 118598868, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3,3-dimethyl-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (1, 0.095 g, 0.32 mmol) in methanol (25 ml), 10% palladium on carbon (25 mg) was added. The reaction mixture was hydrogenated under balloon pressure hydrogen gas for 24 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain a crude residue. The residue was purified by prep HPLC to afford the product as a light yellow solid. Yield: 8.0 mg, 8%; MS (ESI) m/z 298.20 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 8.15 (s, 1H), 7.96 (d, J=7.4 Hz, 1H), 6.81 (d, J=7.5 Hz, 1H), 4.17 (t, J=8.6 Hz, 2H), 3.13 (t, J=8.6 Hz, 2H), 2.59 (s, 2H), 1.79 (s, 6H).

Workup

  1. customAfter complete consumption of starting material, reaction mixture
  2. filtrationwas filtered through a pad of celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain a crude residue
  5. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-f3d6622be20a447fbdc306ab66640306
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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