Dichloromethane → n-(3-Benzylphenyl)-8,9-dihydro-3h-pyrazolo[3,4-c][2,7]naphthyridine-7(6h)-carboxamide

HRID 2383461Notes

Reaction equation

HRID 2383461 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH2+:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.CCN(C(C)C)C(C)C.[CH2:30]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]=[C:44]=[O:45])[CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ClCCl>ClCCCl.O>[CH2:30]([C:37]1[CH:38]=[C:39]([NH:43][C:44]([N:16]2[CH2:15][C:14]3[CH:13]=[N:12][C:11]4[NH:10][N:9]=[CH:8][C:20]=4[C:19]=3[CH2:18][CH2:17]2)=[O:45])[CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 41227751-Benzyl-3-isocyanatobenzeneHCID 866455766,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Product 1

HCID 59490388n-(3-Benzylphenyl)-8,9-dihydro-3h-pyrazolo[3,4-c][2,7]naphthyridine-7(6h)-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of the 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.08 g, 0.2 mmol) in 1,2-dichloroethane (2 mL) was added Hunig's Base (0.2 mL) followed by 1-benzyl-3-isocyanatobenzene (40 μl, 0.2 mmol). The mixture was stirred at room temperature for 2 hours before being diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The organic extracts were dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a pale yellow oil. A minimum amount of dichloromethane was added and N-(3-benzylphenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide crystallized out as a white solid (0.038 g, 36%). M.p.=175-178° C. 1H NMR (DMSO-d6) 400 MHz δ 8.66 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 7.33-7.13 (m, 8H), 6.83 (d, J=7.6 Hz, 1H), 4.75 (s, 2H), 3.88 (s, 2H), 3.80 (d, J=5.2 Hz, 2H). LCMS [M+H]: 384.

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe organic extracts were dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a pale yellow oil
  5. customN-(3-benzylphenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide crystallized out as a white solid (0.038 g, 36%)

Sources & evidence

ORD record
ord-6a4338399cde4ec9974805c3e6ca9554
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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