1,2-Dichloroethane → 6-(2-Oxo-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466180Notes

Reaction equation

HRID 1466180 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([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=2)[CH:24]=[N:23][N:22]=[N:21]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:1]=[C:2]1[CH2:7][N:6]([C:32](=[O:33])[CH2:31][C:28]2[CH:27]=[CH:26][C:25]([N:20]3[CH:24]=[N:23][N:22]=[N:21]3)=[CH:30][CH:29]=2)[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

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 841658(4-Tetrazol-1-yl-phenyl)-acetic acidHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 895334756-(2-Oxo-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (40 mg, 0.16 mmol) and [4-(1H-tetrazol-1-yl)phenyl]acetic acid (38 mg, 0.19 mmol) in DCM (3 ml) was added DMAP (25 mg, 0.20 mmol) and EDC (39 mg, 0.20 mmol). The mixture was allowed to stir at RT for 4 hours. LC showed formation of the desired product. The solvent was removed under vacuum, and the residue was redissolved in methanol, and purified by reverse phase HPLC to give the title product. LC-MS (IE, m/z): 442 [M+1]+.

Sources & evidence

ORD record
ord-8cbbc5982ed0413c8259ded3b38dc718
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…