2-(3-Fluoro-4-nitrophenyl)acetaldehyde → 6-{4-[2-(3-Fluoro-4-nitrophenyl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466137Notes

Reaction equation

HRID 1466137 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1.[F:20][C:21]1[CH:22]=[C:23]([CH2:30][CH:31]=O)[CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28]>>[F:20][C:21]1[CH:22]=[C:23]([CH2:30][CH2:31][N:6]2[CH2:5][CH2:4][N:3]([CH:8]3[CH2:17][CH2:16][C:15]4[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=4[CH2:9]3)[C:2](=[O:1])[CH2:7]2)[CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28]

Participants

3

Reactant 2

HCID 895249042-(3-Fluoro-4-nitrophenyl)acetaldehydeHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 895334686-{4-[2-(3-Fluoro-4-nitrophenyl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Procedure

The title compound was prepared from 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile and (3-Fluoro-4-nitrophenyl)acetaldehyde following essentially the same procedure as Example 6. The product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 411 [M+1]+.

Workup

  1. customThe product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA)

Sources & evidence

ORD record
ord-08dd036414b940a9bcb6160c71056636
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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