Trifluoroacetic acid → HCID 178488911, compound

HRID 1526134Notes

Reaction equation

HRID 1526134 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[C:14]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:15]4[C:16](=[O:31])[NH:17][C:18]5[CH:24]=[C:23]([N:25]6[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]6)[CH:22]=[CH:21][C:19]=5[C:20]=4[C:11]=3[C:10]([CH3:40])=[N:9]2)=CC=1.C(OC(C)C)(C)C.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([C:14]2[C:15]3[C:16](=[O:31])[NH:17][C:18]4[CH:24]=[C:23]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:22]=[CH:21][C:19]=4[C:20]=3[C:11]3[C:10]([CH3:40])=[N:9][NH:8][C:12]=3[N:13]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 136642863HCID 136642863, compound

Product 1

HCID 178488911HCID 178488911, compound

Procedure

A solution of 4.5 g (8.03 mmol) of 3-(4-methoxybenzyl)-5-(4-methoxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one dissolved in 70 ml of trifluoroacetic acid is carried at 70° C. for 4 hours and then cooled to room temperature before the addition of isopropyl ether (150 ml). The reaction medium is stirred at room temperature for 30 minutes and then the precipitate obtained is filtered to yield 5-(4-methoxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one trifluoroacetate. The solid is dissolved in 180 ml of anhydrous dichloroethane. The reaction medium is cooled to 0° C. before the slow addition of 43.3 ml (43.3 mmol) of a 1 M solution of boron tribromide in dichloromethane. The reaction medium is carried at reflux for 7 hours and then cooled again to 0° C. Methanol (approximately 200 ml) is added and then the reaction medium is stirred for 2 hours. The solid obtained is filtered and then triturated several times in hot methanol. A final filtration yields 2.6 g (47%) of 5-(4-hydroxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one hydrobromide in the form of an orange solid.

Workup

  1. customthe precipitate obtained
  2. filtrationis filtered

Sources & evidence

ORD record
ord-188722ba8de346c3a41125a4912b57b1
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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