Acetic Acid → 5-((2-Oxo-4-(2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 1466150Notes

Reaction equation

HRID 1466150 reaction equation
[N:1]1([CH2:7][CH:8]2[CH2:17][CH2:16][CH2:15][C:14]3[C:13]([C:18]#[N:19])=[CH:12][CH:11]=[CH:10][C:9]2=3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:20]=[C:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][CH:31]=O)=[CH:29][C:24]=2[CH2:23][O:22]1.CC(O)=[O:35]>C(Cl)Cl.CO>[O:35]=[C:6]1[CH2:5][N:4]([CH2:31][CH2:30][C:28]2[CH:29]=[C:24]3[C:25](=[CH:26][CH:27]=2)[C:21](=[O:20])[O:22][CH2:23]3)[CH2:3][CH2:2][N:1]1[CH2:7][CH:8]1[CH2:17][CH2:16][CH2:15][C:14]2[C:13]([C:18]#[N:19])=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 675154645-(Piperazin-1-ylmethyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrileHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 895335115-((2-Oxo-4-(2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazin-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 5-(Piperazin-1-ylmethyl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile (30 mg, 0.11 mmol) in 2 mL DCM/MeOH (1/1) was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (0.11 mmol), AcOH (6.6 mg, 0.11 mmol) and the reaction mixture was stirred for 2 hours, and then NaBH3CH (14 mg, 0.22 mmol) was added. The resulting mixture was stirred overnight at ambient temperature. The product was purified by prep-TLC (DCM/MeOH=20:1) to afford the desired product. 1H-NMR (400 MHz, MeOD) δ ppm 7.76 (d, J=8.0 Hz, 1H), 7.44-7.51 (m, 4H), 7.24 (t, J=8.0 Hz, 1H), 5.33 (s, 2H), 3.74-3.80 (m, 1H), 3.32-3.45 (m, 3H), 3.22-3.27 (m, 1H), 3.20 (d, J=2.4 Hz, 2H), 2.96-3.03 (m, 3H), 2.73-2.85 (m, 5H), 1.93-2.02 (m, 1H), 1.75-1.84 (m, 3H).

Workup

  1. additionNaBH3CH (14 mg, 0.22 mmol) was added
  2. stirringThe resulting mixture was stirred overnight at ambient temperature
  3. customThe product was purified by prep-TLC (DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-8cfdee2bd31b4f1393c1d1303fcbae5f
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…