Methanesulfonyl chloride → n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-methanesulfonamide

HRID 720069Notes

Reaction equation

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

Participants

Conditions

Temperature: 22 °C

Procedure

Methanesulfonyl Chloride (1.5 eq, 0.003 g) was added to a solution of the title compound of Example 7 (0.005 g, 0.018 mmol) in CH2Cl2 (0.045 M, 0.4 mL) and pyridine (0.045 M, 0.4 mL). The mixture stirred at 22° C. for 24 hours and concentrated under reduced pressure. Silica gel chromatography (triethylamine/methanol/CH2Cl2; 1:5:94) afforded the title compound (1.7 mg) in 30% yield.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-93f7a0c507734f64851276e7e75484d5
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132533B2

Reaction notes

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