Hydrochloric Acid → 2-[(E)-2-(2-Amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235406Notes

Reaction equation

HRID 2235406 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])([CH3:17])[C:7](=[O:16])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][C:3]=1[NH:19][C:20](=O)/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29].CC(O)C.Cl>O>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[CH:22]=[CH:21]/[C:20]1[NH:19][C:3]2=[CH:4][C:5]3[C:6]([CH3:18])([CH3:17])[C:7](=[O:16])[N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:9]=3[CH:10]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 23092671(E)-N-(6-Amino-3,3-dimethyl-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-amino-phenyl)-acrylamide

Product 1

HCID 593007502-[(E)-2-(2-Amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-N-(6-Amino-3,3-dimethyl-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-amino-phenyl)-acrylamide (0.82 g) is dissolved in water, 2-propanol and concentrated hydrochloric acid and heated for 3 h under reflux. After re-cooling the mixture is concentrated in vacuo. The residue is taken-up in EtOAc and saturated K2CO3 solution. After an aqueous work-up the desired compound (0.73 g) is obtained as a yellow solid. A small amount was treated with hydrochloric acid (2 N) to give the hydrochloric salt which precipitated in a pure form.

Workup

  1. temperatureunder reflux
  2. temperatureAfter re-cooling the mixture
  3. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-8d363ebef11648e88c3d0dae28a43ea4
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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