HCID 136340668, compound → HCID 136340669, compound

HRID 69386Notes

Reaction equation

HRID 69386 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)[N:26]([CH:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)[C:27](=[O:31])[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=[CH:23][C:24]4[CH2:25][N:26]([CH:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)[C:27](=[O:31])[C:28]=4[C:29]([CH3:30])=[C:21]3[N:20]=2)[CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 136340668HCID 136340668, compound

Product 1

HCID 136340669HCID 136340669, compoundYield 15.1%

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 0.12 g of the designed compound as yellowish solid. 1H NMR (500 MHz, DMSO-d6) δ 12.98 (s, 1H, NH), 11.32 (d, J=8.0 Hz, 1H, NH), 11.16 (d, J=4.5 Hz, 1H, NH), 7.80 (s, 1H, ArH), 7.29-7.26 (m, 1H, ArH), 7.15-7.12 (2H, ArH), 6.91-6.85 (m, 1H, ArH), 6.14 (d, J=7.5 Hz, 1H, ArH), 4.43 (s, 2H, CH2), 4.21-4.15 (m, 1H, CH), 4.04-3.99 (m, 1H, CH), 2.97 (d, J=6.5 Hz, 2H, CH2), 2.89-2.87 (m, 2H, CH2), 2.54 (s, 2H, CH2), 2.28 (s, 3H, CH3), 2.21 (s, 3H, CH3), 2.04-1.99 (m, 2H, CH2), 1.89 (s, 3H, CH3), 1.89-1.82 (m, 2H, CH2), 1.70-1.67 (m, 21-1, CH2), 1.34 (d, J=6.0 Hz, 3H, CH3); 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-2254d1b440664870bcfbb78b2284d516
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

Loading…