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

HRID 2383493Notes

Reaction equation

HRID 2383493 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21](=[O:29])[CH2:22][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)=CC=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH:10]1[C:11]2[C:20]3[CH2:19][CH2:18][N:17]([C:21](=[O:29])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 468367751-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

Product 1

HCID 594907491-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanoneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To 1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone (0.203 g, 0.49 mmol) was added trifluoroacetic acid (2 mL). The reaction was heated at 70° C. for 18 hours. To the crude reaction mixture was added toluene (5 mL) and the resulting mixture was evaporated under reduced pressure to give a crude product. The residue was diluted in dichloromethane (4 mL/mmol) and washed with saturated aqueous sodium carbonate. The combined aqueous layers were washed with dichloromethane. The combined organics extract was dried over Na2SO4 and concentrated under reduced pressure to give a brown oil. The oily residue was triturated with a mixture of dichloromethane and methanol to yield the desired product, 1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone as an off-white solid (0.041 g, 18%). M.p.=164-166° C.; 1H NMR (DMSO-d6), 400 MHz) δ 13.57 (s, 1H), 8.36 (s, 1H), 8.12 (s, 1H), 7.27 (m, 5H), 4.87 (s, 1H), 4.77 (s, 1H), 3.82-3.86 (m, 4H), 3.01 (m, 2H); LCMS [M+H]: 293.

Workup

  1. customTo the crude reaction mixture
  2. customthe resulting mixture was evaporated under reduced pressure
  3. customto give a crude product
  4. washwashed with saturated aqueous sodium carbonate
  5. washThe combined aqueous layers were washed with dichloromethane
  6. extractionThe combined organics extract
  7. dry with materialwas dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto give a brown oil
  10. customThe oily residue was triturated with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-185fcd8a597c4581bc14eba522190f63
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…