Trifluoroacetic acid → HCID 46836620, compound

HRID 2383453Notes

Reaction equation

HRID 2383453 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH:21][S:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)(=[O:24])=[O:23])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH:10]1[C:11]2[C:20]3[CH2:19][CH2:18][CH:17]([NH:21][S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:23])=[O:24])[CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67425880HCID 67425880, compound

Product 1

HCID 46836620HCID 46836620, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To N-[3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl]-benzenesulfonamide (0.082 g, 0.18 mmol) was added trifluoroacetic acid (2 mL). The reaction mixture was heated at 65° C. for 5 h. On the completion of the reaction, toluene (5 mL) was added. The solvent was the removed under reduced pressure to give the crude product as a dark brown solid. The crude product was purified using reverse phase HPLC to give the desired product, N-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)benzenesulfonamide was obtained as a white solid (0.038 g, 63%). M.p.=228-229° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.28 (s, 1H), 7.96 (s, 1H), 7.94-7.84 (m, 3H), 7.78 (s, 1H), 7.69-7.58 (m, 3H), 3.48 (br s, 1H), 3.04-2.72 (m, 4H), 1.95-1.7 (m, 2H); LCMS [M+H]: 329.

Workup

  1. additionwas added
  2. customremoved under reduced pressure
  3. customto give the crude product as a dark brown solid
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-839c129535b346789935d8d680487b72
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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