Methanol → HCID 178419700, compound

HRID 1526138Notes

Reaction equation

[NH2:1][C:2]1[C:14]2[C:13]3[C:12]4[CH:15]=[CH:16][C:17]([N:19]5[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]5)=[CH:18][C:11]=4[NH:10][C:9](=[O:32])[C:8]=3[C:7]([C:33]3[CH:38]=[CH:37][C:36]([O:39]C)=[CH:35][CH:34]=3)=[N:6][C:5]=2[NH:4][N:3]=1.B(Br)(Br)[Br:42].CO>ClC(Cl)C>[BrH:42].[NH2:1][C:2]1[C:14]2[C:13]3[C:12]4[CH:15]=[CH:16][C:17]([N:19]5[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]5)=[CH:18][C:11]=4[NH:10][C:9](=[O:32])[C:8]=3[C:7]([C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[N:6][C:5]=2[NH:4][N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 350 mg (0.64 mmol) of tert-butyl 4-(1-amino-5-(4-methoxyphenyl)-6-oxo-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-9-yl)piperazine-1-carboxylate is dissolved in 15 ml of anhydrous dichloroethane. The reaction medium is cooled to −78° C. before the slow addition of 0.30 ml (3.23 mmol) of boron tribromide. The reaction medium is carried at reflux for 4 hours. Methanol (roughly 10 ml) is added at 0° C. and then the reaction medium is stirred at 40° C. for 1 hour. The solid formed is filtered under heat and then rinsed with diethyl ether. Recrystallization of the solid in isopropanol yields 0.26 g (80%) of 1-amino-5-(4-hydroxyphenyl)-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one hydrobromide in the form of a light orange solid.

Workup

temperatureat reflux for 4 hours
customThe solid formed
filtrationis filtered
temperatureunder heat
washrinsed with diethyl ether
customRecrystallization of the solid in isopropanol

Sources & evidence

ORD record: ord-3a8e339625c84db68835526a38b61415
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085575B2

Reaction notes

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