Water → HCID 66686490, compound

HRID 69381Notes

Reaction equation

HRID 69381 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][CH3:11])[C:5]=1[C:12]1[NH:25][C:15]2=[CH:16][C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[C:21]=3[CH:22]=[C:14]2[N:13]=1.[CH3:26]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][CH3:11])[C:5]=1[C:12]1[N:13]([CH3:26])[C:14]2=[CH:22][C:21]3[C:20](=[O:23])[NH:19][C:18](=[O:24])[C:17]=3[CH:16]=[C:15]2[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66687188HCID 66687188, compound

Product 1

HCID 66686490HCID 66686490, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.12 g, 3.04 mmol) was added in portions to a solution of 2-(4-chloro-2-methoxypyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (1.0 g, 3.04 mmol) in 30 mL of anhydrous DMF at 0° C. under argon. The reaction mixture was then stirred at rt for 3 h. MeI (2.16 g, 15.2 mmol) was added dropwise via a syringe at rt under argon. The resulted mixture was stirred for 6 h at rt, hydrolyzed by adding 100 mL of water. The brown precipitate was isolated, washed with water and dried under vacuum. The solid was purified by column chromatography (silica-gel, CH2Cl2/MeOH=49/1 v/v) to give a white solid product, 0.68 g, 65.4% yield. MS: 343.0 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 11.27 (s, 1H), 8.42 (d, 1H, J=5.5 Hz), 8.23 (s, 1H), 8.08 (s, 1H), 7.43 (d, 1H, J=5.5 Hz), 3.89 (s, 3H), 3.75 (s, 3H).

Workup

  1. stirringThe resulted mixture was stirred for 6 h at rt
  2. customThe brown precipitate was isolated
  3. washwashed with water
  4. customdried under vacuum
  5. customThe solid was purified by column chromatography (silica-gel, CH2Cl2/MeOH=49/1 v/v)
  6. customto give a white solid product, 0.68 g, 65.4% yield

Sources & evidence

ORD record
ord-14e45c38850341bab2ec4f205510b518
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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