p-Toluenesulfonic acid monohydrate → HCID 178456639, compound

HRID 2112524Notes

Reaction equation

HRID 2112524 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=O.[NH2:19][C:20]1[C:21]([CH3:29])=[N:22][N:23]([CH2:26][CH:27]=[CH2:28])[C:24]=1Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[C:3]2[CH:4]=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=2[N:1]=[C:24]2[N:23]([CH2:26][CH:27]=[CH2:28])[NH:22][C:21]([CH3:29])=[C:20]2[N:19]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57642323(2-Amino-4,5-dimethylphenyl)-(2-chlorophenyl)-methanoneHCID 576423441-Allyl-5-chloro-3-methyl-1H-pyrazol-4-amine

Product 1

HCID 178456639HCID 178456639, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3.0 g (0.0116 mole) of (2-amino-4,5-dimethylphenyl)-(2-chlorophenyl)-methanone (Xw), 2.0 g (0.0116 mole) of 4-amino-5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole (XIII), 2.21 g (0.0116 mole) of p-toluenesulfonic acid monohydrate and 40 mL of isopropanol was heated in a sealed tube at 170° C. for 90 minutes. The mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and then washed twice with saturated sodium bicarbonate solution. The aqueous washes were reextracted with ethyl acetate, and the combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Trituration of the residue with hexane gave the intermediate 5-(2-chlorophenyl)-1,2-dihydro-3,7,8-trimethyl-1-(2-propenyl)-pyrazolo[3,4-b][1,4]benzodiazepine (XIVw), as a yellow solid. Purification of the filtrates by silica gel chromatography, eluting with ethyl acetate-dichloromethane (1:1) provided additional XIVw and was combined with the material obtained above for a total yield of 2.7 g of XIVw as a yellow solid, which was used directly in the next step.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed twice with saturated sodium bicarbonate solution
  4. dry with materialthe combined ethyl acetate layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bbc71f711f74dc78a2b57c00e14add3
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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