Methyl iodide → HCID 10136533, compound

HRID 1297140Notes

Reaction equation

HRID 1297140 reaction equation
[C:1]1([CH:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]3[CH:20]=[C:21]([O:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[CH:23][C:10]=3[NH:9][C:8]2=[O:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[CH2:32](I)[CH3:33]>>[C:1]1([CH:7]2[N:13]=[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:11]3[CH:20]=[C:21]([O:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[CH:23][C:10]=3[N:9]([CH2:32][CH3:33])[C:8]2=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6340IodoethaneHCID 10221752HCID 10221752, compound

Product 1

HCID 10136533HCID 10136533, compoundYield 65%

Procedure

By replacing 5-(4-bromophenyl)-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIaf) in example IIba by 3,5-diphenyl-8-ethoxy-7-methoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIba), and methyl iodide by ethyl iodide, and proceeding in the same manner, the abovenamed product is obtained. Yield: 65%. M: 178–180° C. 1H-NMR (CDCl3, 300 MHz): d 1.06–1.11 (m, 3H, NCH2CH3), 1.55–1.59 (m, 3H, OCH2CH3), 3.77 (s, 3H, OCH3), 4.19–4.26 (m, 2H, OCH2), 4.01 (AB system, ? d=0.70, JAB=13.7, 2H, NCH2), 6.77 (s, 1H Ar), 6.92 (s, 1H Ar), 7.35–7.74 (m, 10H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom178–180° C

Sources & evidence

ORD record
ord-39b00027173249da85c0626fb3917d86
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…