HCID 136340664, compound → HCID 136340663, compound

HRID 69382Notes

Reaction equation

HRID 69382 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:34])=[C:6]([CH2:8][CH:9]([NH:11][C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=2[C:19]2[NH:33][C:22]3=[CH:23][C:24]4[C:25](=[O:32])[N:26]([CH3:31])[C:27](=O)[C:28]=4[CH:29]=[C:21]3[N:20]=2)[CH3:10])[CH:7]=1>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:34])=[C:6]([CH2:8][CH:9]([NH:11][C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=2[C:19]2[NH:20][C:21]3=[CH:29][C:28]4[CH2:27][N:26]([CH3:31])[C:25](=[O:32])[C:24]=4[CH:23]=[C:22]3[N:33]=2)[CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 136340664HCID 136340664, compound

Product 1

HCID 136340663HCID 136340663, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-(1-(5-Fluoro-2-methylphenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-methyl imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.35 g, 0.76 mmol) and zinc powder (1.20 g, 18.28 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 (100 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, 0.28 g, 82.8% yield. MS: 444.0 [M−H]−. 1H-NMR (DMSO-d6, 300 MHz): δ 13.06 (s, 1H), 11.16 (s, 1H), 11.09-11.06 (m, 1H), 7.95 (s, 0.5H), 7.85 (s, 0.5H), 7.78 (s, 0.5H), 7.69 (s, 0.5H), 7.30-7.10 (m, 3H), 6.91-6.83 (m, 1H), 6.14-6.10 (m, 1H), 4.48 (s, 2H), 4.17-4.13 (m, 1H), 3.10 (s, 3H), 3.03-2.96 (m, 2H), 2.35 (d, 3H, J=4.9 Hz), 1.34-1.32 (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 (100 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, 0.28 g, 82.8% yield

Sources & evidence

ORD record
ord-83e1e50720b94f12a0eb84c9f1eddbd2
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

Loading…