Sodium Sulfite → HCID 66590055, compound

HRID 16814Notes

Reaction equation

HRID 16814 reaction equation
C[Al](C)C.[CH3:5][C:6]1([CH3:23])[NH:11][CH2:10][CH2:9][N:8]([C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=O)=[CH:14][CH:13]=2)[CH2:7]1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][O:35][C:36]2[CH:37]=[C:38]([NH2:41])[NH:39][N:40]=2)[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1.S([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CC(C)=O>[CH3:33][O:32][C:30]1[CH:29]=[C:28]([CH2:34][O:35][C:36]2[CH:37]=[C:38]([NH:41][C:16](=[O:18])[C:15]3[CH:14]=[CH:13][C:12]([N:8]4[CH2:9][CH2:10][NH:11][C:6]([CH3:5])([CH3:23])[CH2:7]4)=[CH:22][CH:21]=3)[NH:39][N:40]=2)[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 16682925TrimethylaluminumHCID 574403815-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amineHCID 57440420Ethyl 4-(3,3-dimethylpiperazin-1-yl)benzoate

Product 1

HCID 66590055HCID 66590055, compoundYield 10.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

A 2M solution of trimethylaluminium in toluene (0.691 mL, 1.38 mmol) was added dropwise to a stirred solution of ethyl 4-(3,3-dimethylpiperazin-1-yl)benzoate (145 mg, 0.55 mmol) and 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine (138 mg, 0.55 mmol) in toluene (5 mL) at 20° C., over a period of 5 mins under nitrogen. The resulting solution was stirred at 20° C. for 24 h. This was diluted with acetone (25 ml) and an excess of damp solid sodium sulphite was added. The mixture was stirred for 1 h and the solid filtered off. The solid was washed with 10% MeOH/DCM and the combined organics evaporated to dryness. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (27.0 mg, 10.49%) as a colourless gum.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationthe solid filtered off
  3. washThe solid was washed with 10% MeOH/DCM
  4. customthe combined organics evaporated to dryness
  5. customThe crude product was purified by preparative HPLC
  6. additionFractions containing the desired compound
  7. customwere evaporated to dryness

Sources & evidence

ORD record
ord-03946f65e1974e919d63fbf74b16581c
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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