Methyl iodide → HCID 9924639, compound

HRID 1297117Notes

Reaction equation

HRID 1297117 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:22][CH2:23][CH3:24])=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)[CH3:2].CI.[CH2:27](I)[CH3:28]>>[CH2:1]([O:3][C:4]1[C:5]([O:22][CH2:23][CH3:24])=[CH:6][C:7]2[N:13]([CH2:27][CH3:28])[C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6340IodoethaneHCID 9858430HCID 9858430, compound

Product 1

HCID 9924639HCID 9924639, compoundYield 59%

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-diethoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIag), and MeI by ethyl iodide, and proceeding in the same manner, the abovenamed product is obtained. Yield: 59%. M: 99–102° C. 1H-NMR (CDCl3, 300 MHz): d 1.11 (t, 3H, CH3), 1.36 (t, 3H, CH3), 1.53 (t, 3H, CH3), 3.93 (q, 2H, OCH2), 3.97 (AB system, ?d=0.67, JAB=14.0, 2H, —NCH2), 4.17 (q, 2H, OCH2), 4.28 (AB system, ?d=0.96 JAB=10.0, 2H, CH2), 6.68 (s, 1H Ar), 6.84 (s, 1H Ar), 7.38–7.64 (m, 5H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom99–102° C

Sources & evidence

ORD record
ord-f1d530684e5d48f5b90fefb3c20f69e9
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…