Methyl iodide → HCID 86760520, compound

HRID 1297119Notes

Reaction equation

HRID 1297119 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.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[CH2:1]([O:3][C:4]1[C:5]([O:22][CH2:23][CH3:24])=[CH:6][C:7]2[N:13]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[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 7748Ethyl bromoacetateHCID 9858430HCID 9858430, compound

Product 1

HCID 86760520HCID 86760520, compoundYield 55%

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 bromoacetate, and proceeding in the same manner, the abovenamed product is obtained. Yield: 55%. M: 160–162° C. 1H-NMR (CDCl3, 200 MHz): d 1.21 (t, 3H, CH3), 1.36 (t, 3H, CH3), 1.50 (t, 3H, CH3), 3.88–4.26 (m, 7H, 3×OCH2+1H CH2) 4.49 (AB system, ? d=0.17, JAB=17.4, 2H, —NCH2), 4.80 (m, 1H CH2), 6.71 (s, 1H Ar), 6.81 (s, 1H Ar), 7.27–7.69 (m, 5H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom160–162° C

Sources & evidence

ORD record
ord-ce2c2396bb5b49bb9d0494dde06003eb
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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