Water → HCID 59490546, compound

HRID 2383416Notes

Reaction equation

HRID 2383416 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH2:17][C:18]5[N:23]([C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)[N:22]=[CH:21][C:19]=5[C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.O.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[C:24]1([N:23]2[C:18]3[CH2:17][CH2:16][C:15]4[CH:14]=[N:13][C:12]5[NH:8][N:9]=[CH:10][C:11]=5[C:20]=4[C:19]=3[CH:21]=[N:22]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 59490646HCID 59490646, compound

Product 1

HCID 59490546HCID 59490546, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-methoxybenzyl)-8-phenyl-3,6,7,8-tetrahydrodipyrazolo[3,4-c:4′,3′-f]isoquinoline (0.7 g, 1.72 mmol) in trifluoroacetic acid (4 mL) was heated at 100° C. for 2 hours. The reaction mixture was poured into water (50 mL) and basified with aqueous potassium carbonate to pH of 11. The reaction mixture was then extracted with dichloromethane (3×75 mL). The combined organic extract was dried using sodium sulfate and concentrated under reduced pressure to give dark residue. The crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform) to give a residue, which was further purified by crystallization from methanol and isopropanol to give the desired product (0.095 g, 18%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.43 (s, 1H), 8.17 (s, 1H), 8.03 (s, 1H), 8.02 (s, 1H), 7.98 (s, 1H), 7.64-7.55 (m, 4H), 7.45 (t, J=3.2 Hz, 1H), 3.12 (s, 4H); LCMS [M+H]: 288.

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane (3×75 mL)
  2. extractionThe combined organic extract
  3. customwas dried
  4. concentrationconcentrated under reduced pressure
  5. customto give dark residue
  6. customThe crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform)
  7. customto give a residue, which
  8. customwas further purified by crystallization from methanol and isopropanol

Sources & evidence

ORD record
ord-1138749ce40f41bcbb3b3451a52f27ef
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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