Triethylamine → ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetate

HRID 2383477Notes

Reaction equation

HRID 2383477 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.CCN(CC)CC.Br[CH:31]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33].C([O-])(O)=O.[Na+]>ClCCl>[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]([CH:31]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97780Ethyl bromophenylacetateHCID 516892Sodium BicarbonateHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 59490451ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.506 g, 1.72 mmol) in dichloromethane (10 mL) and Et3N (0.72 mL, 5.16 mmol) was added ethyl 2-bromo-2-phenylacetate (0.41 mL, 1.89 mmol). The reaction mixture was stirred at room temperature for 16 hours followed by addition of aqueous NaHCO3 (30 mL). The reaction was extracted with EtOAc (60 mL) and the organic layer was then washed with brine (30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2, 50% EtOAc in hexanes) to give the desired product, ethyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylacetate as a yellow solid (0.134 g, 86%). 400 MHz 1H NMR (DMSO-d6) δ 8.25 (s, 1H), 8.10 (s, 1H), 7.5-7.34 (m, 5H), 7.19-7.4 (m, 2H), 6.86-6.8 (m, 2H), 5.76 (s, 1H), 5.56 (s, 2H), 4.46 (s, 1H), 4.13 (q, J=7.2 hz, 2H), 3.76 (s, 2H), 3.69 (s, 3H), 3.05 (t, J=6 hz, 2H), 2.88-2.72 (m, 2H), 1.64 (t, J=7.2 Hz, 3H); LCMS [M+H]:457.5.

Workup

  1. extractionThe reaction was extracted with EtOAc (60 mL)
  2. washthe organic layer was then washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-da08876e3f53459985a2f5557c326fb4
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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