Trifluoroacetic acid → HCID 59490392, compound

HRID 2383428Notes

Reaction equation

HRID 2383428 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH:21]C(=O)OC(C)(C)C)[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH2:21])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59490725HCID 59490725, compound

Product 1

HCID 59490392HCID 59490392, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylcarbamate (3.0 g, 8.8 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 3 hours. The solvent was then removed under reduced pressure to give an oily residue that was triturated in diethyl ether to give a solid. The solid was filtered, washed with diethyl ether and dried under reduced pressure to give the desired product 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylamine (TFA salt) as a brown solid (2.1 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 8.08 (bs, 2H), 8.07 (s, 1H), 8.02 (s, 1H), 7.161 (d, 2H, J=8.4 Hz), 6.84 (d, 2H, J=8.8 Hz), 5.53 (s, 2H), 3.69 (s, 3H), 3.67-3.52 (m, 1H) 3.23 (dd, J=4.4, 16 Hz, 1H), 3.16-3.04 (m, 2H), 2.930 (dd, J=9.6, 15.6 Hz, 1H), 2.19-2.29 (m, 1H), 1.85-1.98 (m, 1H). LCMS [M+H]: 309.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customto give an oily residue that
  3. customwas triturated in diethyl ether
  4. customto give a solid
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-07578b3bd4ef4aa187e67d41e1053cfd
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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