Hydrochloric Acid → HCID 136340674, compound

HRID 69391Notes

Reaction equation

HRID 69391 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[CH:11]=[C:10]3[NH:15][C:16]([C:18]4[C:19]([O:34]C)=[N:20][CH:21]=[CH:22][C:23]=4[O:24][CH:25]([CH3:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:17][C:9]3=[CH:8][C:7]=2[C:6]1=[O:36].Cl>O1CCOCC1>[CH3:37][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[CH:11]=[C:10]3[NH:15][C:16]([C:18]4[C:19](=[O:34])[NH:20][CH:21]=[CH:22][C:23]=4[O:24][CH:25]([CH3:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:17][C:9]3=[CH:8][C:7]=2[C:6]1=[O:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666906826-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 136340674HCID 136340674, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.52 g, 1.04 mmol) was dissolved in 30 mL of 1,4-dioxane at rt. 5 mL of concentrated HCl was added. The reaction mixture was stirred at rt for 12 h. The volatile was removed under reduced pressure. The residue was washed with 20 mL of saturated K2CO3 solution. The pale-yellow precipitate was purified by column chromatography (silica-gel, CH2Cl2/MeOH=7/3 v/v) to give a pale-yellow solid product, 0.38 g, 75.2% yield. MS: 486.8 [M+H]+. 1H-NMR (DMSO-d6, 500 MHz): δ 13.24 (s, 1H), 11.98 (s, 1H), 8.03 (s, 2H), 7.60 (d, 1H, J=7.0 Hz), 7.34-7.32 (m, 2H), 7.12-7.09 (m, 3H), 6.46 (d, 1H, J=7.5 Hz), 4.93-4.87 (m, 1H), 3.70 (t, 2H, J=7.0 Hz), 3.03-2.91 (m, 2H), 2.52 (t, 2H, J=7.0 Hz), 2.19 (s, 6H), 1.27 (d, 3H, J=6.0 Hz).

Workup

  1. customThe volatile was removed under reduced pressure
  2. washThe residue was washed with 20 mL of saturated K2CO3 solution
  3. customThe pale-yellow precipitate was purified by column chromatography (silica-gel, CH2Cl2/MeOH=7/3 v/v)
  4. customto give a pale-yellow solid product, 0.38 g, 75.2% yield

Sources & evidence

ORD record
ord-9968df33e3014a8bbfe8497a413e1aa1
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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