Phenyl isocyanate → HCID 59490421, compound

HRID 2383475Notes

Reaction equation

HRID 2383475 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH2:21])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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][CH:17]([NH:21][C:31]([NH:30][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:32])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 59490392HCID 59490392, compound

Product 1

HCID 59490421HCID 59490421, compoundYield 85.1%

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]isoquinolin-7-ylamine (0.095 g, 0.308 mmol) in dichloromethane (5 mL) was added phenyl isocyanate (37 μL, 0.34 mmol). The reaction mixture was shaken at room temperature for 1 hour. The solvent was removed under reduced pressure and the crude product purified using flash column chromatography (SiO2, gradient from 50% EtOAc in hexane to 66% EtOAc in hexane) to give the desired product, 1-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)-3-phenylurea as a white solid (0.112 g, 84%). Alternative the crude product can be used in the next step without any further purification. M.p. 192-194° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.31 (s, 1H), 8.03 (s, 1H), 7.95 (s, 1H), 7.36 (m, 2H), 7.20 (m, 4H), 6.86 (m, 3H), 6.32 (d, J=7.6 Hz, 1H), 5.54 (s, 2H), 4.05 (m, 1H), 3.70 (s, 3H), 3.17 (m, 1H), 3.08 (m, 3H), 2.81 (m, 1H), 2.11 (m, 1H), 1.89 (m, 1H); LCMS [M+H]: 428.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product purified

Sources & evidence

ORD record
ord-d6269753400d4e789de664c156a50713
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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