HCID 59490674, compound → HCID 46836975, compound

HRID 2383403Notes

Reaction equation

HRID 2383403 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]4[CH2:21][CH2:20][CH2:19][C:18]5[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=5[C:16]4=[C:11]3[CH:10]=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[CH:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]3[CH2:21][CH2:20][CH2:19][C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[C:16]3=2)[NH:8][N:9]=1

Participants

3

Reactant 1

HCID 59490674HCID 59490674, compound

Product 1

HCID 46836975HCID 46836975, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-methoxybenzyl)-3,6,7,8-tetrahydrobenzo[6,7]cyclohepta[1,2-d]pyrazolo[3,4-b]pyridine (2.0 g, 5.63 mmol) in trifluoroacetic acid (10 mL) was heated at 100° C. for 6 hours. On completion of the reaction, the solvent removed under reduced pressure. The residue was dissolved in water (20 mL) and then it was basified to pH=10 using ammonium hydroxide. The aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL). The organic extracts were combined, dried using sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2, gradient 100% dichloromethane to 2% methanol in dichloromethane) to give the pure desired product (0.9 g, 68%) as off-colored solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.58 (s, 1H), 8.14 (s, 1H), 8.10 (s, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.44-7.36 (m, 3H), 7.32 (t, J=8.0 Hz, 1H), 2.60-2.38 (m, 4H), 2.15 (quintet, 3H); LCMS [M+H]: 236.

Workup

  1. customOn completion of the reaction
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. extractionThe aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL)
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-7e19160fd5dd4cf799634b870ba96330
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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