Methyl iodide → HCID 10178209, compound

HRID 1297114Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.CI.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:12]1[C:6]2[CH:5]=[C:4]([O:21][CH3:22])[C:3]([O:2][CH3:1])=[CH:20][C:7]=2[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:9][CH2:10][C:11]1=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 7498Benzyl Bromide

HCID 9965973HCID 9965973, compound

Product 1

HCID 10178209HCID 10178209, compoundYield 64%

Procedure

By replacing 5-(4-bromophenyl)-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIaf) in example IIba by 7,8-dimethoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIaa), and MeI by benzyl bromide, and proceeding in the same manner, the abovenamed product is obtained. Yield: 64%. M: 148–149° C. 1H-NMR (CDCl3, 200 MHz): d 3.67 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.38 (AB system, ? d=0.96, JAB=10.0 2H, CH2), 5.15 (AB system, ? d=0.70, JAB=15.4, 2H, —NCH2), 6.56 (s, 1H Ar), 6.81 (s, 1H Ar), 7.07–7.46 (m, 10H Ar).

Workup

customthe abovenamed product is obtained
custom148–149° C

Sources & evidence

ORD record: ord-ca6dab9094f64efda4439aaa5da04bed
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250410B2

Reaction notes

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