Phenylacetyl chloride → 1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

HRID 2383492Notes

Reaction equation

HRID 2383492 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.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCCl>[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]([C:30](=[O:31])[CH2:29][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 468367751-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.164 g, 0.56 mmol) and 2-phenylacetyl chloride (0.96 mL, 0.724 mmol) was added 1,2-dichloroethane (2 mL). The reaction mixture was stirred at room temperature for 16 hours. The crude reaction mixture was washed with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL). The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the desired product, 1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone as a brown oil (0.230 g, 100%). LCMS [M+H]: 413.

Workup

  1. customThe crude reaction mixture
  2. washwas washed with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a07abeb1ec1c40aa953e5d7d68c3db14
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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