2-(Benzo[c][1,2,5]oxadiazol-5-yl)acetaldehyde → 6-{4-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466129Notes

Reaction equation

HRID 1466129 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.[N:20]1[O:21][N:22]=[C:23]2[CH:28]=[C:27]([CH2:29][CH:30]=O)[CH:26]=[CH:25][C:24]=12>>[N:20]1[O:21][N:22]=[C:23]2[CH:28]=[C:27]([CH2:29][CH2:30][N:6]3[CH2:5][CH2:4][N:3]([CH:8]4[CH2:17][CH2:16][C:15]5[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=5[CH2:9]4)[C:2](=[O:1])[CH2:7]3)[CH:26]=[CH:25][C:24]=12

Participants

3

Reactant 2

HCID 772311582-(Benzo[c][1,2,5]oxadiazol-5-yl)acetaldehydeHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 895334656-{4-[2-(2,1,3-Benzoxadiazol-5-yl)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 2,1,3-benzoxadiazol-5-ylacetaldehyde 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): 402 [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-5787d608b3fc49608d03b76adfcbd511
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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