Triethylamine → 6-{2-Oxo-4-[2-(1-oxo-3,4-dihydro-1H-isochromen-6-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466163Notes

Reaction equation

HRID 1466163 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.C(N(CC)CC)C.[O:27]=[C:28]1[C:37]2[C:32](=[CH:33][C:34]([CH2:38][CH:39]=O)=[CH:35][CH:36]=2)[CH2:31][CH2:30][O:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[O:1]=[C:2]1[CH2:7][N:6]([CH2:39][CH2:38][C:34]2[CH:33]=[C:32]3[C:37](=[CH:36][CH:35]=2)[C:28](=[O:27])[O:29][CH2:30][CH2:31]3)[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

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 772306602-(1-Oxoisochroman-6-yl)acetaldehydeHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 895249856-{2-Oxo-4-[2-(1-oxo-3,4-dihydro-1H-isochromen-6-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (51 mg, 0.17 mmol) and triethylamine (65 mg, 0.64 mmol) was dissolved in dichloroethane then (1-oxo-3,4-dihydro-1H-isochromen-6-yl) acetaldehyde (60 mg, 0.26 mmol) was added followed by sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was stirred at RT for 16 hours. The reaction mixture was poured into water then extracted with dichloromethane. The organic layer was washed with brine then dried over Na2SO4, filtered and concentrated. The compound was purified by preparative TLC plate to yield the title product. 1H-NMR (500 MHz, CDCl3) δ ppm 8.07 (d, J=7.8 Hz, 1H), 7.43 (s, 1H), 7.42 (d, J=7.5 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 7.18 (d, J=7.61 Hz, 1H), 7.14 (s, 1H), 4.90 (b, 1H), 4.57 (t, J=5.7 Hz, 2H), 3.27-3.36 (m, 4H), 3.08 (t, J=5.8 Hz, 2H), 3.02-2.74 (m, 10H), 2.01 (b, 1H), 1.92-1.95 (m, 1H).

Workup

  1. extractionthen extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialthen dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe compound was purified by preparative TLC plate

Sources & evidence

ORD record
ord-f1a8de757cc6459a838b50fc40325b8a
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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