Water → N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383445Notes

Reaction equation

HRID 2383445 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:21]([NH:23][C:24]5[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=5)[C:27]([OH:29])=O)=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[Cl-].Cl[CH:46]1[N:50](C)CC[NH+:47]1C.O.[CH3:54][C:55](N(C)C)=[O:56]>ClCCl>[O:56]1[CH:55]=[CH:54][C:46]([NH:50][C:27]([C:26]2[CH:25]=[C:24]([NH:23][C:21]([N:17]3[CH2:16][C:15]4[CH:14]=[N:13][C:12]5[NH:8][N:9]=[CH:10][C:11]=5[C:20]=4[CH2:19][CH2:18]3)=[O:22])[CH:32]=[CH:31][CH:30]=2)=[O:29])=[N:47]1.[O:56]1[CH:55]=[CH:54][C:46]([NH:50][C:27]([C:26]2[CH:25]=[C:24]([NH:23][C:21]([N:17]3[CH2:16][C:15]4[CH:14]=[N:13][C:12]5[N:8]([CH2:7][C:6]6[CH:33]=[CH:34][C:3]([O:2][CH3:1])=[CH:4][CH:5]=6)[N:9]=[CH:10][C:11]=5[C:20]=4[CH2:19][CH2:18]3)=[O:22])[CH:32]=[CH:31][CH:30]=2)=[O:29])=[N:47]1

Participants

8

Reactant 5

HCID 962WaterHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 594904523-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid

Product 2

HCID 59490647N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamideHCID 67426873N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamido)benzoic acid (0.037 g, 80 μmol), isoxa-3-ylamine (8.8 μL, 120 μmol) and Hunig's Base (71 μL, 400 μmol) in dimethylacetamide (1 mL) and dichloromethane (1 mL) was added 2-chloro-1,3-dimethylimidazolinium chloride (DMC, 0.041 g, 240 μmol). The reaction mixture was shaken at room temperature for 16 hours followed by addition of water (2 mL) and dichloromethane (4 mL) were added. The organic layer was separated and the solvent removed under reduced pressure to give the desired product, N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide. LCMS [M+H]: 524. The crude product was used in the next step without any further purification.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7772c0e498844e1da2c3a167e379eed7
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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