Trifluoroacetic acid → HCID 59490623, compound

HRID 2383469Notes

Reaction equation

HRID 2383469 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([CH2:21][C:22]5[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=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>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N: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)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59490448HCID 59490448, compound

Product 1

HCID 59490623HCID 59490623, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To 3,7-bis-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.092 g, 0.22 mmol) was added trifluoroacetic acid (3 mL). The reaction mixture was heated at 65° C. for 16 hours. On the completion of the reaction, toluene (5 mL) was added. The solvent was removed under reduced pressure to give a dark brown solid. The residue was then partitioned between EtOAc and aqueous NaOH. The organic layer was then separated, washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified using flash column chromatography (SiO2, 1% methanol in EtOAc) to desired product, 7-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine as a pale yellow solid (0.047 g, 72%). M.p.=184-186° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.49 (s, 1H), 8.19 (s, 1H), 8.08 (s, 1H), 7.32-7.26 (m, 2H), 6.94-6.88 (m, 2H), 3.75 (s, 3H), 3.64 (s, 2H), 3.62 (s, 2H), 3.1-3.03 (m, 2H), 2.8-2.72 (m, 2H); LCMS [M+H]: 295.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customto give a dark brown solid
  4. customThe residue was then partitioned between EtOAc and aqueous NaOH
  5. customThe organic layer was then separated
  6. washwashed with brine (2×10 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue
  11. customThe crude product was purified

Sources & evidence

ORD record
ord-6a43b0effdba4aed9a6323816cf3cc41
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…