1-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-[1,4]diazepan-5-one → 1-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-4-((R)-2-oxiranyl-ethyl)-[1,4]diazepan-5-one

HRID 1867377Notes

Reaction equation

HRID 1867377 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[F:8].C[C:22]1(C)[O:26][C@H:25]([CH2:27][CH2:28]OS(C)(=O)=O)CO1>>[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[CH2:22][O:26]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 620467621-[(E)-3-(3-Chloro-4-fluoro-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 866158661-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-4-((R)-2-oxiranyl-ethyl)-[1,4]diazepan-5-one

Procedure

In analogy to the procedure described for example 172A to 172C, 1-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 54) and methanesulfonic acid 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester gave the title compound as pink oil. MS: 367.0 (MH+, 1Cl).

Sources & evidence

ORD record
ord-556de157133246f0825d878f22f5a6ac
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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