Phenyl isocyanate → 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383455Notes

Reaction equation

HRID 2383455 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([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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]([C:30]([NH:29][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[O:31])[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 7672Phenyl isocyanateHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 594905663-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

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 (0.075 g, 0.256 mmol) in dichloromethane (3 mL) was added phenyl isocyanate (31 μL, 0.281 mmol). The reaction mixture was shaken at room temperature for 1 hour. The solvent was then removed under reduced pressure to give 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a tan solid (LCMS [M+H]:414), which was used for next step without further purification. White solid; M.p.=>65° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.72 (s, 1H), 8.41 (s, 1H), 8.20 (s, 1H), 7.51-7.45 (m, 2H), 7.28-7.15 (m, 4H), 6.98-6.91 (m, 1H), 6.88-6.82 (m, 2H), 5.59 (s, 2H), 4.79 (s, 2H), 3.82 (t, 6.4 hz, 2H), 3.67 (s, 3H), 3.14 (t, J=J=6.4 Hz, 2H); LCMS [M+H]: 414.6.

Workup

  1. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-d4115e93383241a6a0171724e9db2f16
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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