Methyl iodide → 3-benzyl-8-ethoxy-1-ethyl-7-methoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1297113Notes

Reaction equation

HRID 1297113 reaction equation
[CH2:1]([CH:8]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]2[CH:21]=[C:22]([O:28][CH3:29])[C:23]([O:25][CH2:26][CH3:27])=[CH:24][C:11]=2[NH:10][C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[CH2:33](I)[CH3:34]>>[CH2:1]([CH:8]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]2[CH:21]=[C:22]([O:28][CH3:29])[C:23]([O:25][CH2:26][CH3:27])=[CH:24][C:11]=2[N:10]([CH2:33][CH3:34])[C:9]1=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6340IodoethaneHCID 69461618HCID 69461618, compound

Product 1

HCID 694588793-benzyl-8-ethoxy-1-ethyl-7-methoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneYield 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-benzyl-8-ethoxy-7-methoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIbb), and methyl iodide by ethyl iodide, and proceeding in the same manner, the abovenamed product is obtained. Yield: 65%. F: 228–230° C. 1H-NMR (CDCl3, 300 MHz): d 1.03–1.08 (m, 3H, NCH2CH3), 1.50–1.54 (m, 3H, OCH2CH3), 3.59–3.65 (m, 3H, 1HNCH2+CH2Bn), 3.70 (s, 3H, OCH3), 3.77–3.83 (m, 1H, 1CH), 4.12–4.18 (m, 2H, OCH2), 4.30–4.41 (m, 1H, 1HNCH2), 6.62 (s, 1H Ar), 6.79 (s, 1H Ar), 7.22–7.59 (m, 10H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom228–230° C

Sources & evidence

ORD record
ord-d1af6bd00a8c4d1eab08b447453164c5
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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