Triethylamine → HCID 89533483, compound

HRID 1466164Notes

Reaction equation

HRID 1466164 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)[CH:31]=[CH: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][CH:30]=[CH: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 77230658(1-oxo-1H-isochromen-6-yl)acetaldehydeHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 89533483HCID 89533483, compound

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 (26 mg, 0.089 mmol) and triethylamine (12.1 mg, 0.12 mmol) was dissolved in dichloroethane (10 ml) then (1-Oxo-1H-isochromen-6-yl) acetaldehyde (15 mg, 0.080 mmol) followed by sodium triacetoxyborohydride (51 mg, 0.24 mmol) was added. The reaction mixture was stirred at RT for 16 hrs. The reaction mixture was poured into water and extracted with DCM. 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 8.27 (d, J=8.1 Hz, 1H), 7.43 (s, 1H), 7.42 (d, J=8.5 Hz, 2H), 7.32 (d, J=5.7 Hz, 1H), 7.19 (d, J=7.8 Hz, 1H), 6.50 (d, J=5.8 Hz, 1H), 4.90 (b, 1H), 3.28-3.39 (m, 4H), 2.92-3.03 (m, 6H), 2.76-2.86 (m, 4H), 2.04 (b, 1H), 1.89-1.98 (m, 1H).

Workup

  1. additionwas added
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was purified by preparative TLC plate

Sources & evidence

ORD record
ord-dd760da37dc643dfb18eca2b79b39fa5
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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