Water → N-(5-Ethyl-7,7-dimethyl-6-oxo-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-benzamide

HRID 2235462Notes

Reaction equation

HRID 2235462 reaction equation
[NH2:1][C:2]1[NH:18][C:5]2=[CH:6][C:7]3[C:8]([CH3:17])([CH3:16])[C:9](=[O:15])[N:10]([CH2:13][CH3:14])[C:11]=3[CH:12]=[C:4]2[N:3]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>N1C=CC=CC=1>[CH2:13]([N:10]1[C:11]2[CH:12]=[C:4]3[N:3]=[C:2]([NH:1][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:18][C:5]3=[CH:6][C:7]=2[C:8]([CH3:17])([CH3:16])[C:9]1=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 593007322-Amino-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 59301003N-(5-Ethyl-7,7-dimethyl-6-oxo-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-benzamideYield 67.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of D3 (500 mg) and benzoyl chloride (0.6 ml; 5.12 mmol) in pyridine (15 ml) is stirred at RT for 20 h. After completion, water is added and the aqueous layer is extracted with EtOAc. The combined organic layer is washed with hydrochloric acid (1 N), saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (30:1) afford the title compound (484 mg).

Workup

  1. extractionthe aqueous layer is extracted with EtOAc
  2. washThe combined organic layer is washed with hydrochloric acid (1 N), saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (30:1)

Sources & evidence

ORD record
ord-6c03aad9a03242828c32febf77e7b17b
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…