HCID 136338244, compound → HCID 178434384, compound

HRID 1526136Notes

Reaction equation

HRID 1526136 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[C:14]([C:25]4[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=4)[C:15]4[CH2:16][NH:17][C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=5[C:20]=4[C:11]=3[C:10]([CH3:33])=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[CH3:33][C:10]1[C:11]2[C:20]3[C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=[CH:16][C:15]=3[C:14]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[N:13][C:12]=2[NH:8][N:9]=1

Participants

3

Reactant 1

HCID 136338244HCID 136338244, compound

Product 1

HCID 178434384HCID 178434384, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 350 mg (0.75 mmol) of 3-(4-methoxybenzyl)-5-(4-methoxyphenyl)-1-methyl-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridine dissolved in 15 ml of trifluoroacetic acid is carried at 70° C. for 4 hours and then cooled to room temperature. The solvents are evaporated and then water is added. The product is extracted with ethyl acetate; the organic phases are dried on magnesium sulfate and concentrated. The residue is triturated in acetonitrile. The solid is filtered and then dissolved in 20 ml of anhydrous dichloroethane. The reaction medium is cooled to 0° C. before the slow addition of 7 ml (7 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 is added until the reaction medium is completely homogenized. The solvents are evaporated and then the residue is purified several times by silica gel chromatography (eluent: 95:5 DCM/MeOH) to yield 32 mg (15%) of 4-(1-methyl-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-5-yl)phenol in the form of a brown solid.

Workup

  1. customThe solvents are evaporated
  2. additionwater is added
  3. extractionThe product is extracted with ethyl acetate
  4. customthe organic phases are dried on magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is triturated in acetonitrile
  7. filtrationThe solid is filtered
  8. dissolutiondissolved in 20 ml of anhydrous dichloroethane
  9. temperatureThe reaction medium is cooled to 0° C. before the slow addition of 7 ml (7 mmol) of a 1 M solution of boron tribromide in dichloromethane
  10. temperatureat reflux for 7 hours
  11. temperaturecooled again to 0° C
  12. additionMethanol is added until the reaction medium
  13. customThe solvents are evaporated
  14. customthe residue is purified several times by silica gel chromatography (eluent: 95:5 DCM/MeOH)

Sources & evidence

ORD record
ord-a250ee2dfc9248b8b51932a16b36d0ec
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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