Sodium → 6-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}naphthalene-2-carbonitrile

HRID 1465785Notes

Reaction equation

HRID 1465785 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=[CH:12]2.[O:21]=[C:22]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][CH:32]=O)=[CH:30][C:25]=2[CH2:24][O:23]1.[Na]>C(O)(=O)C.C(Cl)Cl>[O:2]=[C:3]1[CH2:8][N:7]([CH2:32][CH2:31][C:29]2[CH:28]=[CH:27][C:26]3[C:22](=[O:21])[O:23][CH2:24][C:25]=3[CH:30]=2)[CH2:6][CH2:5][N:4]1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=[CH:12]2

Participants

6

Reactant 3

HCID 5360545SodiumHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 895251926-(2-Oxopiperazin-1-yl)naphthalene-2-carbonitrile hydrochloride

Product 1

HCID 715256896-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}naphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 25 mL pear shaped flask charged with 6-(2-Oxopiperazin-1-yl)naphthalene-2-carbonitrile hydrochloride [I-5] (30 mg, 0.10 mmol) and a stir bar was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde [I-1] (28 mg, 0.16 mmol), sodium triacetocyborohydride (22 mg, 0.10 mmol), DCM, and a few drops of acetic acid. The mixture was allowed to stir at RT for 16 hours. The title product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 412 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-e7134ab073804fb5a045395bb15f9e2e
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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