HCID 118598905, compound → HCID 118598943, compound

HRID 1050331Notes

Reaction equation

HRID 1050331 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([N:17]3[C:18](=[O:29])[C:19]([NH:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][N:24]=4)=[CH:20][CH:21]=[C:16]3[C:15](=[O:30])[NH:14]2)[CH2:9]1)C1C=CC=CC=1>O1CCOCC1.Cl>[N:26]1[CH:27]=[CH:28][C:23]([NH:22][C:19]2[C:18](=[O:29])[N:17]3[C:10]4([NH:14][C:15](=[O:30])[C:16]3=[CH:21][CH:20]=2)[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)=[N:24][CH:25]=1

Participants

4

Reactant 1

HCID 118598905HCID 118598905, compound

Product 1

HCID 118598943HCID 118598943, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of l′-benzyl-6-(pyrimidin-4-ylamino)-1H-spiro[imidazo[1,5-a]pyridine-3,3′-piperidine]-1,5(2H)-dione (5, 0.12 g, 0.29 mmol) in dioxane (1 mL), 4 M hydrogenchloride in dioxane (2 mL) was added at 0° C. and the reaction mixture was stirred at room temperature for 3 h. The solvent was removed under reduced pressure and the residue was purified by repeated washing with pentane. Compound was dissolved in water and passed through strata column to obtain 6-(pyrimidin-4-ylamino)-1H-spiro[imidazo[1,5-a]pyridine-3,3′-piperidine]-1,5(2H)-dione (Cpd. No. 20) as a light brown solid. Yield: 0.062 g, 67%; MS (ESI) m/z 313.15 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.13 (s, 1H), 9.40 (s, 1H), 8.80-8.73 (m, 2H), 8.38 (d, J=5.9 Hz, 1H), 7.37 (dd, J=5.9, 1.3 Hz, 1H), 6.89 (d, J=7.7 Hz, 1H), 3.94 (d, J=12.5 Hz, 1H), 3.16-3.12 (m, 1H), 2.95 (d, J=13.1 Hz, 1H), 2.74-2.65 (m, 1H), 2.60 (s, 1H), 2.46 (d, J=11.7 Hz, 1H), 1.72 (d, J=8.2 Hz, 2H), 1.61 (d, J=13.0 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified
  3. washby repeated washing with pentane
  4. dissolutionCompound was dissolved in water

Sources & evidence

ORD record
ord-58253abd7a5340d0bf3a9cf45b7a6ab5
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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