N-{3-[2-(7,7-dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide → 2-[2-(3-Amino-phenyl)-ethyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235411Notes

Reaction equation

HRID 2235411 reaction equation
[CH3:1][C:2]1([CH3:32])[C:10]2[CH:9]=[C:8]3[NH:11][C:12]([CH2:14][CH2:15][C:16]4[CH:17]=[C:18]([NH:22]C(=O)C)[CH:19]=[CH:20][CH:21]=4)=[N:13][C:7]3=[CH:6][C:5]=2[N:4]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:3]1=[O:31]>CC(O)C.Cl>[NH2:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][C:12]2[NH:11][C:8]3=[CH:9][C:10]4[C:2]([CH3:32])([CH3:1])[C:3](=[O:31])[N:4]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:5]=4[CH:6]=[C:7]3[N:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 59300739N-{3-[2-(7,7-dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide

Product 1

HCID 593009062-[2-(3-Amino-phenyl)-ethyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A solution of N-{3-[2-(7,7-dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-ethyl]-phenyl}-acetamide (70 mg) in 2-propanol (1 ml) and hydrochloric acid (6 M; 1 ml) is heated under reflux for 3.5 h. Afterwards the mixture is concentrated in vacuo and the residual aqueous layer is neutralized with saturated NaHCO3 solution. The desired compound is obtained by an aqueous work-up (47 mg).

Workup

  1. temperatureunder reflux for 3.5 h
  2. concentrationAfterwards the mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-b1c4f6a771ef4b16be4f221b5af8da46
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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