2-(4-(1-(2,3,5,6-Tetrafluorophenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione → HCID 136340662, compound

HRID 69380Notes

Reaction equation

HRID 69380 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH2:11][CH:12]([NH:14][C:15]1[CH:20]=[CH:19][NH:18][C:17](=[O:21])[C:16]=1[C:22]1[NH:36][C:25]2=[CH:26][C:27]3[C:28](=[O:35])[N:29]([CH3:34])[C:30](=O)[C:31]=3[CH:32]=[C:24]2[N:23]=1)[CH3:13]>C(O)(=O)C.[Zn]>[CH3:34][N:29]1[CH2:30][C:31]2[CH:32]=[C:24]3[NH:23][C:22]([C:16]4[C:17](=[O:21])[NH:18][CH:19]=[CH:20][C:15]=4[NH:14][CH:12]([CH3:13])[CH2:11][C:3]4[C:4]([F:10])=[C:5]([F:9])[CH:6]=[C:7]([F:8])[C:2]=4[F:1])=[N:36][C:25]3=[CH:26][C:27]=2[C:28]1=[O:35]

Participants

4

Reactant 1

HCID 1363406612-(4-(1-(2,3,5,6-Tetrafluorophenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 136340662HCID 136340662, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-(1-(2,3,5,6-Tetrafluorophenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.51 g, 1.02 mmol) and zinc powder (1.60 g, 24.51 mmol) were suspended in acetic acid (30 mL). The reaction mixture was stirred and heated to reflux overnight under argon. Then, the solvent was removed under reduced pressure. The residue solid was stirred in 100 mL of saturated K2CO3 solution. The white solid was filtered out, dried under vacuum and extracted with CH2Cl2/MeOH (7/3 v/v) three times (300 mL). The extracts were concentrated to dryness. The residue was purified by column chromatography (silica-gel, CH2Cl2/MeOH=9/1 v/v) to give a pale-yellow solid product, 0.31 g, 62.6% yield. MS: 508.0 [M+Na]+. 1H NMR (DMSO-d6, 500 MHz): δ 13.03 (s, 1H), 11.24 (s, 1H), 11.14-11.11 (m, 1H), 7.95 (s, 0.5H), 7.78-7.74 (m, 2H), 7.61 (s, 0.5H), 7.35 (s, 1H), 6.15 (s, 1H), 4.48 (s, 2H), 4.22 (m, 1H), 3.17-3.10 (m, 2H), 3.09 (s, 3H), 1.37 (m, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight under argon
  3. customThen, the solvent was removed under reduced pressure
  4. stirringThe residue solid was stirred in 100 mL of saturated K2CO3 solution
  5. filtrationThe white solid was filtered out
  6. customdried under vacuum
  7. extractionextracted with CH2Cl2/MeOH (7/3 v/v) three times (300 mL)
  8. concentrationThe extracts were concentrated to dryness
  9. customThe residue was purified by column chromatography (silica-gel, CH2Cl2/MeOH=9/1 v/v)
  10. customto give a pale-yellow solid product, 0.31 g, 62.6% yield

Sources & evidence

ORD record
ord-915c3c0c0a1e4a9f933f03661f0785c0
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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