1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,4]diazepan-5-one

HRID 1867440Notes

Reaction equation

HRID 1867440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][C:22]1([CH3:34])[O:26][C@H:25]([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:24][O:23]1>>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:28][CH2:27][C@@H:25]3[CH2:24][O:23][C:22]([CH3:34])([CH3:21])[O:26]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one2×HCID 86615867methanesulfonic acid 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Product 1

HCID 684319871-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,4]diazepan-5-one

Procedure

In analogy to the procedure described for example 167A, 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 1A]) and methanesulfonic acid 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (prepared from 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol and methanesulfonyl chloride) gave after reaction at RT, the title compound as an off-white foam. MS: 441.1 (MH+, 2Cl).

Workup

  1. customgave
  2. customafter reaction at RT

Sources & evidence

ORD record
ord-fb6c81bf8963481c92c97bf53b62d513
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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