Cyanogen Bromide → 2-Amino-1-isopropyl-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo [4,5-f]indol-6-one

HRID 2235460Notes

Reaction equation

HRID 2235460 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][CH:20]([CH3:22])[CH3:21].Br[C:24]#[N:25]>O.C1COCC1>[NH2:25][C:24]1[N:19]([CH:20]([CH3:21])[CH3:22])[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 2

HCID 10476Cyanogen BromideHCID 674272526-Amino-5-isopropylamino-3,3-dimethyl-1-pentyl-1,3-dihydro-indol-2-one

Product 1

HCID 593007422-Amino-1-isopropyl-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo [4,5-f]indol-6-oneYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Analogously to general procedure (III) 6-amino-5-isopropylamino-3,3-dimethyl-1-pentyl-1,3-dihydro-indol-2-one (180 mg) is cyclized using BrCN (3 M; 0.2 ml; 600 μmol) at RT in water (2.5 ml) and THF (1 ml). After aqueous work-up the desired compound (190 mg) is obtained.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-e154b16468964f978dcde395dd92d022
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…