Toluene → 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

HRID 2383425Notes

Reaction equation

HRID 2383425 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][NH:17][CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.C1(C)C=CC=CC=1.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>>[F:30][C:31]([F:36])([F:35])[C:32]([O-:34])=[O:33].[CH:10]1[C:11]2[C:20]3[CH2:19][CH2:18][NH2+:17][CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:8][N:9]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 866455766,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Procedure

A solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (1.90 g, 6.46 mmol) in trifluoroacetic acid (20 mL) was heated at 65° C. for 16 hours. On completion of the reaction, toluene (10 mL) was added and the reaction mixture evaporated to dryness under reduced pressure to give the desired product as a dark brown gel. The crude product was triturated with 1,4-dioxane. The resulting solid was filtered to give the desired product, 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate as a tan powder (2.52 g, 97%)

Workup

  1. additionwas added
  2. customthe reaction mixture evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-45bbf6997dc64f118f7c19b8caba310a
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…