HCID 136340645, compound → 8-Methyl-6-(1-methylpiperidin-4-yl)-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)-6,7-dihydroimidazo[4,5-f]isoindol-5(3H)-one

HRID 920481Notes

Reaction equation

HRID 920481 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=O)[N:8]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[C:7](=[O:19])[C:6]=2[CH:5]=[C:4]2[NH:20][C:21]([C:23]3[C:24](=[O:43])[NH:25][CH:26]=[CH:27][C:28]=3[NH:29][CH:30]([CH3:42])[CH2:31][C:32]3[C:37]([F:38])=[C:36]([F:39])[CH:35]=[C:34]([F:40])[C:33]=3[F:41])=[N:22][C:3]=12>[Zn].C(O)(=O)C>[CH3:1][C:2]1[C:10]2[CH2:9][N:8]([CH:12]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]3)[C:7](=[O:19])[C:6]=2[CH:5]=[C:4]2[NH:20][C:21]([C:23]3[C:24](=[O:43])[NH:25][CH:26]=[CH:27][C:28]=3[NH:29][CH:30]([CH3:42])[CH2:31][C:32]3[C:33]([F:41])=[C:34]([F:40])[CH:35]=[C:36]([F:39])[C:37]=3[F:38])=[N:22][C:3]=12

Participants

4

Reactant 1

HCID 136340645HCID 136340645, compound

Product 1

HCID 1363406478-Methyl-6-(1-methylpiperidin-4-yl)-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)-6,7-dihydroimidazo[4,5-f]isoindol-5(3H)-oneYield 11%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-methyl-6-(1-methylpiperidin-4-yl)-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.93 g, 1.65 mmol), zinc dust (1.02 g, 15.6 mmol), and 30 mL of acetic acid was heated at reflux for 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 0.10 g (11.0%) of the designed compound as yellowish solid. 1H NMR (500 MHz, DMSO-d6) δ 12.93 (s, 1H, NH), 11.28 (d, J=8.5 Hz, 1H, NH), 11.23 (d, J=4.1 Hz, 1H, NH), 7.75 (m, 1H, ArH), 7.60 (s, 1H, ArH), 7.36 (m, 1H, ArH), 6.19 (d, J=8.0 Hz, 1H, ArH), 4.40 (s, 2H, CH2), 4.28 (m, 1H, CH), 3.99 (m, 1H, CH), 3.07 (m, 2H, CH2), 2.88-2.84 (m, 2H, CH2), 2.74 (s, 3H, CH3), 2.20 (s, 3H, CH3), 2.02-1.98 (m, 2H, CH2), 1.82-1.80 (m, 2H, CH2), 1.67 (m, 2H, CH2), 1.36 (d, J=6.0 Hz, 3H, CH3); Mass (ESI, positive) m/z 583.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-80c3bd3266d746f08725f5b2c6d7549a
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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