Toluene → Trifluoroacetic acid

HRID 2383466Notes

Reaction equation

HRID 2383466 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]>>[CH:10]1[C:11]2[C:20]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:8][N:9]=1.[C:32]([OH:34])([C:31]([F:36])([F:35])[F:30])=[O:33]

Participants

5

Reactant 3

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

Product 2

HCID 6422Trifluoroacetic acidHCID 46836771HCID 46836771, compound

Procedure

A solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.14 g, 0.47 mmol) in trifluoroacetic acid (2 mL) was heated at 65° C. for 16 hours. On completion of the reaction, toluene (5 mL) was added. The solvent was then removed under reduced pressure to give a dark brown solid. The solvent was removed under reduced pressure to give 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a TFA salt. LCMS [M+H]: 175.

Workup

  1. additionwas added
  2. customThe solvent was then removed under reduced pressure
  3. customto give a dark brown solid
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-770e730236cc4625b6b775bc50f498bd
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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