Acetic Acid → HCID 136340672, compound

HRID 69389Notes

Reaction equation

HRID 69389 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][N:5]1[CH2:13][C:12]2[CH:11]=[C:10]3[NH:14][C:15]([C:17]4[C:18](=[O:35])[NH:19][CH:20]=[CH:21][C:22]=4[NH:23][CH:24]([CH3:34])[CH2:25][C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=4[CH3:33])=[N:16][C:9]3=[C:8]([CH3:36])[C:7]=2[C:6]1=O.C(O)(=[O:41])C>[Zn]>[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][N:5]1[CH2:6][C:7]2[C:8]([CH3:36])=[C:9]3[N:16]=[C:15]([C:17]4[C:18](=[O:35])[NH:19][CH:20]=[CH:21][C:22]=4[NH:23][CH:24]([CH3:34])[CH2:25][C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=4[CH3:33])[NH:14][C:10]3=[CH:11][C:12]=2[C:13]1=[O:41]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1363406736-(2-(dimethylamino)ethyl)-2-(4-(1-(5-fluoro-2-methylphenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6,7-dihydroimidazo[4,5-f]isoindol-5(1H)-one

Product 1

HCID 136340672HCID 136340672, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 6-(2-(dimethylamino)ethyl)-2-(4-(1-(5-fluoro-2-methylphenyl)propan-2-ylamino)-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6,7-dihydroimidazo[4,5-f]isoindol-5(1H)-one (0.27 g, 0.51 mmol), zinc dust (0.33 g, 5.09 mmol), and 8.5 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 517.2 [M+H]+, 539.2 [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-5cdd7d35ad79472585390ac33af3b113
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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