Trifluoroacetic acid → Trifluoroacetic acid

HRID 2383471Notes

Reaction equation

HRID 2383471 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:18][C:17]2[CH:16]=[N:15][C:14]3[N:19](CC4C=CC(OC)=CC=4)[N:20]=[CH:21][C:13]=3[C:12]=2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][CH:9]1[CH2:18][C:17]2[CH:16]=[N:15][C:14]3[NH:19][N:20]=[CH:21][C:13]=3[C:12]=2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([OH:35])([C:32]([F:37])([F:36])[F:31])=[O:34]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59490853HCID 59490853, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 46836619HCID 46836619, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To N-benzyl-3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-amine (0.030 g, 0.075 mmol) was added trifluoroacetic acid (3 mL). The reaction mixture was heated at 65° C. for 2 hours. On completion of the reaction, toluene (2 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC to give the desired product, N-benzyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-amine as a TFA salt and a white solid (0.015 g, 71%). M.p.>232° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.39 (s, 1H), 9.06 (brs, 2H), 8.05 (d, J=1.6 Hz, 1H), 7.99 (s, 1H), 7.56 (m, 2H), 7.46 (m, 3H), 4.31 (s, 2H), 3.61 (m, 1H), 3.43 (m, 1H), 3.08 (m, 3H), 2.43 (m, 1H), 1.97 (m, 1H); LCMS [M+H]: 279.

Workup

  1. additionwas added
  2. customthe solvent removed under reduced pressure
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-b0de389eeda54e83bc3505c616aae38d
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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