1,1'-Carbonyldiimidazole → HCID 59497484, compound

HRID 1747380Notes

Reaction equation

HRID 1747380 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([NH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]2[NH:13][C:28](=[O:29])[N:14]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:9]=2[CH:8]=1)=[O:22])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497419HCID 59497419, compound

Product 1

HCID 59497484HCID 59497484, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Amino-3-(2-Ethoxycarbonyl-ethylamino)-benzoic acid tert-butyl ester (900 mg, 2.92 mmol) in THF (20 ml) was added CDI (997 mg, 6 mmol). The solution was heated at 90 degrees for 30 minutes. The reaction mixture was evaporated to dryness, and then taken up in Ethyl Acetate. The organic phase was washed with brine, dried over MgSO4, filtered, evaporated to dryness. The residue was purified by flash Chromatography eluded with 5% methanol in CH2Cl2. After evaporation of the desired fractions, 800 mg was obtained (82%).

Workup

  1. temperatureThe solution was heated at 90 degrees for 30 minutes
  2. customThe reaction mixture was evaporated to dryness
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash Chromatography
  8. customAfter evaporation of the desired fractions
  9. custom800 mg was obtained (82%)

Sources & evidence

ORD record
ord-5f1ed1d307174f9188a44c805963ee5e
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…