Benzenesulfonyl chloride → 3-(4-methoxybenzyl)-7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

HRID 2383450Notes

Reaction equation

HRID 2383450 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.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>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]([S:36]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)(=[O:38])=[O:37])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 594906193-(4-methoxybenzyl)-7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridineYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.129 g, 0.43 mmol) in dichloromethane (8 mL) and Et3N (0.13 mL, 0.86 mmol) was added benzenesulfonyl chloride (62 μL, 0.47 mmol). The reaction mixture was shaken at room temperature for 1 hour. The solvent was then removed under reduced pressure and the residue obtained was partitioned between EtOAc and aqueous NaOH. The organic layer was then separated, washed with brine (2×10 mL), concentrated under reduced pressure. The crude product was purified using either flash column chromatography (SiO2, 33% EtOAc in hexane) to give 3-(4-methoxybenzyl)-7-(phenylsulfonyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a white solid (0.147 g, 77%) or used in the next step without any further purification. M.p.=136-138° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.39 (s, 1H), 8.12 (s, 1H), 7.88-7.83 (m, 2H), 7.72-7.59 (m, 3H), 7.18-7.13 (m, 2H), 6.86-6.8 (m, 2H), 5.55 (s, 2H), 4.36 (s, 2H), 3.68 (s, 3H), 3.43, t, J=6.4 Hz, 2H), 3.13 (t, J=6.4 Hz, 2H), 2.54-2.48 (m, 2H); LCMS [M+H]: 435.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue obtained
  3. customwas partitioned between EtOAc and aqueous NaOH
  4. customThe organic layer was then separated
  5. washwashed with brine (2×10 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-93e74c23d5dd410ea4abb0f4afbc8437
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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