Hydrochloric Acid → HCID 10142877, compound

HRID 970106Notes

Reaction equation

HRID 970106 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3[CH2:21][N:22]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:24][C:19]=3[N:18]([CH2:28][CH:29]([OH:44])[CH2:30][N:31]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH3:43])[CH2:33][CH2:32]3)[N:17]=2)=[CH:12][C:11]=1[N+:45]([O-])=O.Cl.C(=O)(O)[O-].[Na+]>O.C1COCC1>[NH2:45][C:11]1[CH:12]=[C:13]([C:16]2[C:20]3[CH2:21][N:22]([C:25](=[O:27])[CH3:26])[CH2:23][CH2:24][C:19]=3[N:18]([CH2:28][CH:29]([OH:44])[CH2:30][N:31]3[CH2:32][CH2:33][N:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH3:43])[CH2:35][CH2:36]3)[N:17]=2)[CH:14]=[CH:15][C:10]=1[Cl:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 17975413HCID 17975413, compound

Product 1

HCID 10142877HCID 10142877, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium hydrosulfite (1.28 g, 7.3 mmol) in 30 mL water was added 1-{3-(4-chloro-3-nitro-phenyl)-1-[2-hydroxy-3-(4-o-tolyl-piperazin-1-yl)-propyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-ethanone (810 mg, 1.5 mmol) in 15 mL THF. The reaction mixture was stirred at room temperature for 5 min. The color of the solution changed from light yellow to colorless. Hydrochloride solution (1 N, 10 mL) was added to the reaction mixture. This solution was stirred at room temperature for 30 min, and treated with saturated sodium bicarbonate until the pH of the solution between 7 to 8. The product was extracted with dichloromethane (3×80 mL). The organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to a residue. This residue was purified by column chromatography (silica, 5-20% MeOH/CH2Cl2) to afford 644 mg (84.1%) of the title compound. MS (electrospray): m/z 523.3 (523.3, calculated for C28H35ClN6O2, [M+H]+). 1H NMR (CDCl3, 400 MHz, a mixture of two rotamers): 7.30-6.70 (m, 7H), 4.80-4.60 (m, 1H), 4.55 (s, 1H), 4.20-4.05 (m, 4H), 3.95-3.90 (m, 2H), 3.80-3.60 (m, 2H), 2.90-2.30 (m, 9H), 2.20 (s, 3H), 2.15 (s, 1.5H), 2.10 (s, 1.5H).

Workup

  1. stirringThis solution was stirred at room temperature for 30 min
  2. extractionThe product was extracted with dichloromethane (3×80 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure to a residue
  5. customThis residue was purified by column chromatography (silica, 5-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-26e02f6b56df4b65b32d5df44c40a1dd
Source dataset
uspto-grants-2007_12
Patent number
US07309703B2

Reaction notes

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