HCID 59490356, compound → HCID 59490577, compound

HRID 2383489Notes

Reaction equation

HRID 2383489 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([C:21]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[C:24]1([NH:23][C:21]([CH:17]2[CH2:16][C:15]3[CH:14]=[N:13][C:12]4[NH:8][N:9]=[CH:10][C:11]=4[C:20]=3[CH2:19][CH2:18]2)=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 59490356HCID 59490356, compound

Product 1

HCID 59490577HCID 59490577, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-Methoxybenzyl)-N-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline-7-carboxamide in trifluoroacetic acid (5 mL) was heated at 65° C. for 8 hours. The mixture was evaporated to dryness and partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate (100 mL). The organic layer was dried with anhydrous magnesium sulfate and evaporated under reduced pressure the residue obtained was triturated with dichloromethane (2 mL) to give N-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline-7-carboxamide as a white powder (10 mg). M.p.=>300° C. 1H NMR (DMSO-d6) 400 MHz δ 13.30 (s, 1H), 10.05 (s, 1H), 8.0 (s, 1H), 7.95 (s, 1H), 7.63 (d, J=7.6 Hz, 2H), 7.31 (t, J=7.6 Hz, 2H), 7.04 (t, J=7.6 Hz, 1H), 3.09-3.00 (m, 4H), 2.96-2.81 (m, 1H), 2.19-2.17 (m, 1H), 2.03-1.93 (m, 1H). LCMS [M+H]: 293.

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate (100 mL)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customevaporated under reduced pressure the residue
  5. customobtained
  6. customwas triturated with dichloromethane (2 mL)

Sources & evidence

ORD record
ord-a9874afbebf44ce7ab936fa9324efcf0
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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