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

HRID 44579Notes

Reaction equation

HRID 44579 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-dadf252f37d94dd1afe4d1bc2f6dd87f
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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