HCID 118598903, compound → HCID 118598605, compound

HRID 1050332Notes

Reaction equation

HRID 1050332 reaction equation
[O:1]=[C:2]1[C:20]2=[CH:21][CH:22]=[C:23]([NH:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][N:28]=3)[C:24](=[O:25])[N:19]2[C:4]2([CH2:8][CH2:7][N:6](C(OCC3C=CC=CC=3)=O)[CH2:5]2)[NH:3]1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[N:30]1[CH:31]=[CH:32][C:27]([NH:26][C:23]2[C:24](=[O:25])[N:19]3[C:4]4([NH:3][C:2](=[O:1])[C:20]3=[CH:21][CH:22]=2)[CH2:8][CH2:7][NH:6][CH2:5]4)=[N:28][CH:29]=1

Participants

4

Reactant 1

HCID 118598903HCID 118598903, compound

Product 1

HCID 118598605HCID 118598605, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of benzyl 1,5-dioxo-6-(pyrimidin-4-ylamino)-2,5-dihydro-1H-spiro[imidazo[1,5-a]pyridine-3,3′-pyrrolidine]-1′-carboxylate (5, 0.06 g, 0.138 mmol) in ethyl acetate:methanol (10:1, 33 mL), 20% palladium hydroxide (0.03 g) was added. The reaction mixture was hydrogenated under balloon pressure for 4 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC and repeated washing with ether to afford 6-(pyrimidin-4-ylamino)-1H-spiro[imidazo[1,5-a]pyridine-3,3′-pyrrolidine]-1,5(2H)-dione (Cpd. No. 26) as a white solid. Yield: 0.025 g, 60%; MS (ESI) m/z 299.20 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.47 (s, 1H), 8.83-8.74 (m, 2H), 8.38 (d, J=5.9 Hz, 1H), 7.37 (d, J=5.9 Hz, 1H), 6.92 (d, J=7.7 Hz, 1H), 3.67 (d, J=12.6 Hz, 1H), 3.19-3.03 (m, 2H), 2.95-2.75 (m, 2H), 2.05-1.88 (m, 1H).

Workup

  1. customAfter complete consumption of starting material
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative TLC
  5. washrepeated washing with ether

Sources & evidence

ORD record
ord-2213f6ae7c974587ab7d1d6f62215772
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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