Water → HCID 59300775, compound

HRID 2235429Notes

Reaction equation

HRID 2235429 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][C:3]=1[NH:15][C:16](=O)[CH2:17][CH2:18][C:19]1[NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=1.O>C(O)(=O)C>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[CH2:18][CH2:17][C:16]1[NH:15][C:3]2=[CH:4][C:5]3[C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]([CH3:11])[C:9]=3[CH:10]=[C:2]2[N:1]=1

Participants

4

Reactant 2

HCID 962WaterHCID 23092653HCID 23092653, compound

Product 1

HCID 59300775HCID 59300775, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(6-amino-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-3-(1H-benzoimidazol-2-yl)-propionamide (218 mg) in acetic acid (6 ml) is heated under reflux for 3 h. After re-cooling, water is added and the mixture is extracted with EtOAc (3×30 ml). The combined organic layer is washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give the desired compound (90 mg).

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter re-cooling
  3. extractionthe mixture is extracted with EtOAc (3×30 ml)
  4. washThe combined organic layer is washed with saturated NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2fee304b1b74ff6bd71e5a0ed234772
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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