Triethylamine → HCID 59490448, compound

HRID 2383468Notes

Reaction equation

HRID 2383468 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][NH:17][CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[CH3:23]CN(CC)CC.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[OH-].[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([CH2:23][C:37]5[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=5)[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 115693-MethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 59490448HCID 59490448, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.125 g, 0.425 mmol) in dichloroethane (5 mL) and Et3N (0.18 mL, 1.27 mmol) was added 3-methoxybenzaldehyde (57.3 μL, 0.467 mmol) followed by tetramethylammonium triacetoxyborohydride (0.33 g, 1.27 mmol). The reaction mixture was shaken at room temperature 56 hours followed by the addition of 1.5M NaOH (10 mL). The reaction mixture was shaken at room temperature for 1 hour. The reaction mixture was than extracted with EtOAc (30 mL). The organic layer was washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified using flash column chromatography (SiO2, gradient from 50% EtOAc in hexanes to 66% EtOAc in hexane) to give the desired product, 3,7-bis(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a pale yellow solid (0.119 g, 67%). M.p.=105-107° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.25 (s, 1H), 8.11 (s, 1H), 7.28 (d, J=8.4 hz, 2H), 7.17 (d, J=8 Hz, 2H), 6.91 (d, J=8 Hz, 2H), 6.83 (d, J=8.8 hz, 2H), 5.56 (s, 2H), 3.75 (s, 3H), 3.69 (s, 3H), 3.68-3.6 (m, 4H), 3.12-3.03 (m, 2H), 2.82-2.73 (m, 2H); LCMS [M+H]: 415.

Workup

  1. stirringThe reaction mixture was shaken at room temperature for 1 hour
  2. extractionthan extracted with EtOAc (30 mL)
  3. washThe organic layer was washed with brine (2×10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-a6d1813149844bc7b670768aaad1f80d
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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