4-Pyridinemethanamine → 6,7-Dimethoxy-4-{4-[2-nitro-1-(4-pyridylmethylamino)vinyl]-1-piperazinyl}quinazoline

HRID 2230092Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21](SC)=[CH:22][N+:23]([O-:25])=[O:24])[CH2:17][CH2:16]1.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[CH:22][N+:23]([O-:25])=[O:24])[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a pyridine solution (10 mL) of Compound 58 produced in Example 58 (730 mg, 1.87 mmol), 4-aminomethylpyridine (0.57 mL, 5.61 mmol) was added, followed by stirring in argon atmosphere under heating at 80° C. for 5 hours. After the reaction solution was allowed to stand for cooling, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography to give the target compound (130 mg, 0.29 mmol).

Workup

temperaturefor cooling
customthe solvent was evaporated
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fa23113b099d493c89eb601015ca31e3
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423716B1

Reaction notes

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