Hydrochloric Acid → Ethyl 8-ethoxy-1-methyl-4,5-dihydro-1h-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 875087Notes

Reaction equation

HRID 875087 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15]([CH3:18])(=O)=O)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:3]1.[CH:24]1[CH:29]=[CH:28]C(S)=[CH:26][CH:25]=1.[OH-:31].[Na+].Cl>C(O)C>[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15][C:18]4[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=4)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:3]1.[CH2:29]([O:31][C:11]1[N:10]=[CH:9][C:8]2[CH2:7][CH2:6][C:5]3[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:3][N:2]([CH3:1])[C:14]=3[C:13]=2[N:12]=1)[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 57531759HCID 57531759, compound

Product 2

HCID 57444090Ethyl 8-ethoxy-1-methyl-4,5-dihydro-1h-pyrazolo[4,3-h]quinazoline-3-carboxylateHCID 57531739HCID 57531739, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of ethyl 1-methyl-8-(methylsulfonyl)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (46 mg, 0.137 mmol) and phenylthiol (16 μl, 17 mg, 0.15 mmol) in ethanol (1 mL), 1N sodium hydroxide (150 μl, 0.15 mmol) was added at room temperature under an argon atmosphere. After the mixture was stirred for 3 days, 1N hydrochloric acid (150 μl, 0.15 mmol) was added and the solvent removed under vacuo. By chromatography on silica gel (eluant: dichloromethane/methanol 97/3), 13 mg of ethyl 1-methyl-8-(phenylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate and 10 mg of ethyl 8-ethoxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate were isolated.

Workup

  1. additionwas added at room temperature under an argon atmosphere
  2. customthe solvent removed under vacuo

Sources & evidence

ORD record
ord-ffaa72d1c7c2468e872e444b8a42f754
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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