4-Methoxybenzylamine → HCID 86649116, compound

HRID 1471026Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:25]2[CH:30]=[CH:29][C:28](Cl)=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:25]2[CH:30]=[CH:29][C:28]([NH:42][CH2:41][C:40]3[CH:43]=[CH:44][C:37]([O:36][CH3:35])=[CH:38][CH:39]=3)=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 145 °C

Procedure

The product from Example 179C (13.2 g, 27.5 mmol) and 4-methoxybenzylamine (18 mL, 139 mmol) were combined and stirred at 145° C. for 1.5 h. The mixture was cooled to rt, and CH2Cl2 was added. The resulting precipitate was filtered off, and the filtrate was washed successively with 1N aq. HCl and saturated aq. NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-25% EtOAc in hexane to give the title compound (5.0 g, 31%).

Workup

temperatureThe mixture was cooled to rt
filtrationThe resulting precipitate was filtered off
washthe filtrate was washed successively with 1N aq. HCl and saturated aq. NaHCO3
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-25% EtOAc in hexane

Sources & evidence

ORD record: ord-c7bd46f3b26540c68cbf51d8435053b7
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006387B2

Reaction notes

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