Trifluoroacetic acid → HCID 59490394, compound

HRID 2383473Notes

Reaction equation

HRID 2383473 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH:21][C:22](=[O:29])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[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][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59490723HCID 59490723, compound

Product 1

HCID 59490394HCID 59490394, compoundYield 25%

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]-benzamide (0.084 g, 0.21 mmol) was added trifluoroacetic acid (2 mL). The reaction mixture was heated at 65° C. for 16 hours. On completion of the reaction, toluene (5 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-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)benzamide as a white solid (0.015 g, 25%). M.p.>300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.31 (s, 1H), 8.49 (d, J=7.2 Hz, 1H), 8.00 (d, J=1.2 Hz, 1H), 7.92 (s, 1H), 7.86 (m, 2H), 7.48 (m, 3H), 4.28 (m, 1H), 3.22-2.91 (m, 4H), 2.13 (m, 1H), 1.96 (m, 1H); LCMS [M+H]: 293.

Workup

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

Sources & evidence

ORD record
ord-0f9d046f2511477eb37aa799745ef86d
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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