Piperazine → Methyl 2-(6-(tert-butoxycarbonylamino)-5-fluoropyridin-3-yloxy)-4-(piperazin-1-yl)benzoate

HRID 624401Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[CH:25]=[C:24](F)[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:11][C:10]=1[F:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.ClCCl>CS(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[CH:25]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:11][C:10]=1[F:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

Methyl 2-(6-(tert-butoxycarbonylamino)-5-fluoropyridin-3-yloxy)-4-fluorobenzoate (0.170 g) and piperazine (0.154 g) were dissolved in dimethylsulfoxide (2 mL) and heated to 85° C. After 1 hour, the reaction was cooled, poured into dichloromethane (75 mL), and washed with water (30 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to give the title compound.

Workup

temperaturethe reaction was cooled
washwashed with water (30 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-622988570b7147ce8bdf9de752764fb1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303025B2

Reaction notes

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