Benzoyl chloride → N-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-N-methyl-benzamide

HRID 2235469Notes

Reaction equation

[CH3:1][C:2]1([CH3:32])[C:10]2[CH:9]=[C:8]3[N:11](S(C4C=CC(C)=CC=4)(=O)=O)[C:12]([NH:14][CH3:15])=[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].[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:32])[C:10]2[CH:9]=[C:8]3[NH:11][C:12]([N:14]([CH3:15])[C:33](=[O:40])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 7,7-dimethyl-2-methylamino-5-pentyl-1-(toluene-4-sulfonyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (120 mg) in pyridine (5 ml) is added drop-wise benzoyl chloride (0.1 ml; 0.79 mmol) at 0° C. After addition the mixture is heated at 130° C. for 5 h. An aqueous work-up and purification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (40:1) yield the desired compound (38 mg).

Workup

additionAfter addition the mixture
customAn aqueous work-up and purification by flash chromatography on silica gel eluting with CH2Cl2/MeOH (40:1)

Sources & evidence

ORD record: ord-5c2fe22a4b3240ac8e5a8b319935da85
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714010B2

Reaction notes

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