Succinic anhydride → HCID 59456977, compound

HRID 1362208Notes

Reaction equation

HRID 1362208 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([N:12]([CH3:24])[CH2:13][C:14]2[N:15]([CH3:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:11])=[CH:4][CH:3]=1.[C:25]1(=O)[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>O1CCOCC1>[O:29]=[C:28]1[CH2:27][CH2:26][C:25](=[O:30])[N:1]1[C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH3:24])[CH2:13][C:14]2[N:15]([CH3:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 4473613HCID 4473613, compound

Product 1

HCID 59456977HCID 59456977, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(6-aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (1.40 g, 4.37 mol) and succinic anhydride (520 mg, 5.24 mmol) in 1,4-dioxane (50 mL) was heated to reflux for 5 h. Another portion of succinic anhydride (520 mg, 5.24 mmol) was then added, and the solution was maintained at reflux overnight. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2, and the solution was washed with satd NaHCO3, water and brine, dried over Na2SO4, and concentrated. Purification by column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 97:3) gave the title compound (1.40 g, 76%) as an off-white solid and as a mixture of amide rotamers: mp 185-187° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.92-8.88 (m, 1H), 8.41-8.32 (m, 1H), 7.69-7.64 (m, 1H), 7.52-7.34 (m, 4H), 7.15-7.09 (m, 1H), 7.04-6.99 (m, 1H), 6.44-6.21 (m, 1H), 5.08-4.87 (m, 2H), 3.73-3.70 (m, 3H), 3.14-3.00 (m, 3H), 2.83-2.81 (m, 4H); MS (ESI) m/e 403 (M+H)+.

Workup

  1. temperatureto reflux for 5 h
  2. temperaturethe solution was maintained
  3. temperatureat reflux overnight
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washthe solution was washed with satd NaHCO3, water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customPurification by column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 97:3)

Sources & evidence

ORD record
ord-6e7e444d50b14635baa3fa555665edb6
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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