Diisopropylethylamine → HCID 136340645, compound

HRID 69352Notes

Reaction equation

HRID 69352 reaction equation
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:30][C:12]2=[CH:13][C:14]3[C:15](=[O:29])[N:16]([CH:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[C:17](=[O:21])[C:18]=3[C:19]([CH3:20])=[C:11]2[N:10]=1.[F:31][C:32]1[C:37]([F:38])=[CH:36][C:35]([F:39])=[C:34]([F:40])[C:33]=1[CH2:41][CH:42]([NH2:44])[CH3:43].CCN(C(C)C)C(C)C>C(O)CCC>[CH3:20][C:19]1[C:18]2[C:17](=[O:21])[N:16]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[C:15](=[O:29])[C:14]=2[CH:13]=[C:12]2[NH:30][C:9]([C:3]3[C:4](=[O:8])[NH:5][CH:6]=[CH:7][C:2]=3[NH:44][CH:42]([CH3:43])[CH2:41][C:33]3[C:34]([F:40])=[C:35]([F:39])[CH:36]=[C:37]([F:38])[C:32]=3[F:31])=[N:10][C:11]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 866632171-(2,3,5,6-Tetrafluorophenyl)propan-2-amineHCID 1362003242-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 136340645HCID 136340645, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (1.00 g, 2.35 mmol), 1-(2,3,5,6-tetrafluorophenyl)propan-2-amine (0.54 g, 2.58 mmol), Hunig's base (1.52 g, 0.011 mol), and 20 mL of anhydrous 1-butanol was heated at reflux for 14-15 h under an argon atmosphere. Product was purified by a silica gel column using methylene chloride and methanol (9:1 v/v) as eluent to afford 1.10 g of the designed compound as yellowish solid. 1H NMR (500 MHz, DMSO-d6) δ 13.35 (s, 1H, NH), 11.35 (d, J=6.0 Hz, 1H, NH), 11.02 (d, J=8.5 Hz, 1H, NH), 7.93 (s, 1H, ArH), 7.81-7.77 (m, 1H, ArH), 7.42 (t, J=7.0 Hz, 1H, ArH), 6.22 (d, J=8.0 Hz, 1H, ArH), 4.34-4.29 (m, 1H, CH), 4.12 (m, 1H, CH), 3.17 (m, 2H, CH2), 3.08 (d, J=5.5 Hz, 21-1, CH2), 2.72 (s, 3H, CH3), 2.48 (s, 3H, CH3), 1.77-1.76 (m, 2H, CH2), 1.37 (d, J=6.5 Hz, 3H, CH3), 1.29-1.24 (m, 6H, 2×CH2); Mass (ESI, positive) m/z 597.2 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 14-15 h under an argon atmosphere
  3. customProduct was purified by a silica gel column

Sources & evidence

ORD record
ord-a7c52bd83085462da55984a22513159f
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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