HCID 136340668, compound → HCID 136340670, compound

HRID 69387Notes

Reaction equation

HRID 69387 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[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:40][C:22]3=[CH:23][C:24]4[C:25](=[O:39])[N:26]([CH:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)[C:27](=O)[C:28]=4[C:29]([CH3:30])=[C:21]3[N:20]=2)[CH3:10])[CH:7]=1>[Zn].C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[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:40][C:22]3[C:21]([N:20]=2)=[C:29]([CH3:30])[C:28]2[CH2:27][N:26]([CH:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[C:25](=[O:39])[C:24]=2[CH:23]=3)[CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 136340668HCID 136340668, compound

Product 1

HCID 136340670HCID 136340670, compoundYield 3.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(4-(1-(5-fluoro-2-methylphenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.81 g, 1.46 mmol), zinc dust (0.95 g, 14.55 mmol), and 25 mL of acetic acid was heated at reflux for 13-14 h under an argon atmosphere. Product was separated by a silica gel column using methylene chloride and methanol (85:15 v/v) as eluent to afford 30 mg of the designed compound as yellowish solid. 1H NMR (500 MHz, DMSO-d6) δ; Mass (ESI, positive) m/z 543.2 [M+H]+, 565.2 [M+Na]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 13-14 h under an argon atmosphere
  3. customProduct was separated by a silica gel column

Sources & evidence

ORD record
ord-046239474a794d739323299b9ff3eb96
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

Loading…