HCID 118599106, compound → HCID 118598671, compound

HRID 1050330Notes

Reaction equation

HRID 1050330 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1([CH3:31])[N:17]2[C:18](=[O:29])[C:19]([NH:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][N:24]=3)=[CH:20][CH:21]=[C:16]2[C:15](=[O:30])[NH:14]1>CO.O.NN>[NH2:3][CH2:12][C:13]1([CH3:31])[N:17]2[C:18](=[O:29])[C:19]([NH:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][N:24]=3)=[CH:20][CH:21]=[C:16]2[C:15](=[O:30])[NH:14]1

Participants

4

Reactant 1

HCID 118599106HCID 118599106, compound

Product 1

HCID 118598671HCID 118598671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

To a solution of 3-((1,3-dioxoisoindolin-2-yl)methyl)-3-methyl-6-(pyrimidin-4-ylamino)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (5, 0.085 g, 0.29 mmol) in methanol (20 mL), hydrazine hydrate (2 mL) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water, separated, dried over sodium sulphate and concentrated under reduced pressure, which was purified by repeated washing with diethyl ether and hexane to obtain 3-(aminomethyl)-3-methyl-6-(pyrimidin-4-ylamino)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (Cpd. No. 15) as an off-white solid. Yield: 0.008 g, 9%; MS (ESI) m/z 287.05[M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.35 (s, 1H), 8.76 (d, J=7.8 Hz, 2H), 8.36 (d, J=5.9 Hz, 1H), 7.36 (d, J=6.0 Hz, 1H), 6.83 (d, J=7.6 Hz, 1H), 3.55 (d, J=13.6 Hz, 1H), 2.92 (d, J=13.7 Hz, 1H), 1.75 (s, 3H), 1.44 (s, 1H), 1.41-1.34 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. customseparated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure, which
  8. customwas purified
  9. washby repeated washing with diethyl ether and hexane

Sources & evidence

ORD record
ord-27de7b135e6944ad83d1a54c61927366
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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